CN115403505A - Preparation method of thioester compound containing indolone structure - Google Patents
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- CN115403505A CN115403505A CN202211072242.2A CN202211072242A CN115403505A CN 115403505 A CN115403505 A CN 115403505A CN 202211072242 A CN202211072242 A CN 202211072242A CN 115403505 A CN115403505 A CN 115403505A
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- -1 thioester compound Chemical class 0.000 title claims abstract description 55
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical group C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 10
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 8
- 239000011733 molybdenum Substances 0.000 claims abstract description 8
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims abstract description 6
- 229910000024 caesium carbonate Inorganic materials 0.000 claims abstract description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims abstract description 6
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical group C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 5
- 239000003446 ligand Substances 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 2
- 239000002585 base Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 abstract description 7
- 239000011593 sulfur Substances 0.000 abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000003638 chemical reducing agent Substances 0.000 abstract description 4
- 239000000758 substrate Substances 0.000 abstract description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005810 carbonylation reaction Methods 0.000 description 4
- 150000005624 indolones Chemical class 0.000 description 4
- 238000005936 thiocarbonylation reaction Methods 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- VRIBZFMVQAWISS-UHFFFAOYSA-N [Mo][C]=O Chemical compound [Mo][C]=O VRIBZFMVQAWISS-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FGFUBBNNYLNVLJ-UHFFFAOYSA-N indolone Natural products C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention discloses a preparation method of thioester compound containing indolone structure, which comprises the following steps: reacting palladium acetate, tricyclohexylphosphine, molybdenum carbonyl, cesium carbonate, water, iodo-aromatic hydrocarbon and sulfonyl chloride compound at 100 ℃ for 24 hours, and after the reaction is completed, carrying out post-treatment to obtain the thioester compound containing the indolone structure. The reaction raw materials are cheap and easy to obtain, the substrate applicability is good, the reaction efficiency is high, and meanwhile, the molybdenum carbonyl is used as a carbonyl source and a reducing agent, so that the operation is simple. In addition, the method takes sulfonyl chloride compounds as sulfur sources, and provides a new way for constructing thioester compounds containing indolone structures.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of a thioester compound containing an indolone structure.
Background
Indolones are a very important class of heterocyclic molecules, widely found in a variety of natural products, bioactive molecules and drugs (eur.j. Med. Chem.2021,216, 113334). In addition, indolone has a very wide application in organic synthesis as a key reaction intermediate. Thus, various methods for synthesizing indolones have been developed. The most attractive approach is based on a transition metal-catalyzed cascade cyclization reaction, since the organometallic complexes formed in the reaction can be converted further to give functionalized indolone derivatives.
In recent years, transition metal catalyzed carbonylation reactions have made significant progress both in academic and industrial areas as an important process for the synthesis of carbonyl-containing compounds (Chem 2019,5, 526). Indolone derivatives can also be constructed by transition metal catalyzed cyclization/carbonylation reactions. Among these reactions, the synthesis of thioester compounds containing an indolone structure has attracted a wide attention because thioester compounds are considered as a class of organic compounds having unique chemical properties in life sciences and synthetic chemistry. However, there are very limited reports on the synthesis of thioester compounds containing an indolone structure. Therefore, it is necessary to explore more reaction pathways for constructing thioester compounds containing indolone structures.
In recent years, transition metal catalyzed thiocarbonylation reactions have become an important tool for the synthesis of thioester compounds. In most thiocarbonylation reactions, mercaptans are generally used as a sulfur source, and have certain limitations because of their strong thiophilic properties to transition metals, which tend to poison the catalyst (chem. Rev.1989,89, 1). Therefore, the development of carbonylation reactions based on alternative sulfur sources remains one of the major efforts of chemists. Sulfonyl chloride is used as a chemical reagent which is cheap and easy to obtain and simple to operate, and has very important application in organic synthesis. In recent years, a series of thiocarbonylation reactions using sulfonyl chlorides as a sulfur source have been developed by us team. Therefore, on the basis of previous work, we developed a palladium-catalyzed cyclization/thiocarbonylation reaction to synthesize thioester compounds containing an indolone structure. It is noteworthy that sulfonyl chlorides as an important sulfur source in the reaction, both aryl and alkyl substituted sulfonyl chlorides, are well compatible with the reaction. Meanwhile, molybdenum carbonyl is used as a carbonyl source and a reducing agent, so that the method has a good application prospect.
Disclosure of Invention
The invention provides a preparation method of thioester compound containing indolone structure, which has cheap and easily obtained reaction raw materials, good substrate applicability and high reaction efficiency, and simultaneously, molybdenum carbonyl is used as both carbonyl source and reducing agent, thus the operation is simple. In addition, the method takes sulfonyl chloride compounds as sulfur sources, provides a new way for constructing thioester compounds containing indolone structures, and highlights the application of the sulfonyl chloride compounds in carbonylation reactions.
A preparation method of thioester compound containing indolone structure comprises the following steps: reacting a palladium catalyst, tricyclohexylphosphine, molybdenum carbonyl, cesium carbonate, water, iodo aromatic hydrocarbon and a sulfonyl chloride compound at 90-110 ℃ for 20-28 hours, and after the reaction is completed, carrying out post-treatment to obtain the thioester compound containing the indolone structure;
the structure of the iodo-aromatic hydrocarbon is shown as the formula (II):
the sulfonyl chloride compound has a structure shown in a formula (III):
R 4 -SO 2 Cl (III)；
the structure of the thioester compound containing the indolone structure is shown as the formula (I):
in formulae (I) to (III), R 1 Is H, C 1 ～C 4 Alkyl, trifluoromethyl or halogen;
R 2 is C 1 ～C 4 Alkyl or p-toluenesulfonyl;
R 3 is H or C 1 ～C 7 A hydrocarbyl group;
R 4 is C 1 ～C 6 Alkyl radical, C 1 ～C 6 Cycloalkyl or substituted phenyl, the substituent on the phenyl being C 1 ～C 4 Alkyl, methoxy, phenyl.
The molar ratio of the palladium catalyst, tricyclohexylphosphine and cesium carbonate is 0.01;
R 1 the substitution positions of (a) are para and meta.
The reaction formula is as follows:
in the present invention, the optional post-processing procedure includes: filtering, mixing a sample with silica gel, and finally performing column chromatography purification to obtain a corresponding thioester compound containing an indolone structure, wherein the column chromatography purification is a technical means commonly used in the field.
Preferably, R 1 Is H, methyl, tert-butyl, trifluoromethyl, F or Br; r is 2 Is methyl, ethyl, n-butyl or p-toluenesulfonyl; r 3 Is methyl or benzyl. At this time, the iodoaromatic hydrocarbon is easily available and the yield of the reaction is high.
Preferably, R 4 Is cyclohexyl or substituted phenyl, and the substituent on the phenyl is methyl, isopropyl, tertiary butyl, methoxyl or phenyl. In this case, the sulfonyl chloride compound is easily obtained, and the yield of the reaction is high.
The iodo aromatic hydrocarbon and sulfonyl chloride compounds used for preparing thioester compounds containing an indolinone structure are relatively inexpensive and widely exist in nature, and preferably, the iodo aromatic hydrocarbon: sulfonyl chloride compound: the palladium catalyst =1: 0.05 to 0.1; as a further preference, the molar amount of iodoaromatic hydrocarbon: sulfonyl chloride compound: palladium catalyst = 1.5.
Preferably, the reaction time is 24 hours, and if the reaction time is too long, the reaction cost is increased, and conversely, it is difficult to ensure the completion of the reaction.
Preferably, the reaction is carried out in N, N-dimethylformamide in an amount sufficient to dissolve the starting material, and about 1 to 2mL of N, N-dimethylformamide is used as 0.2mmol of the iodoaromatic hydrocarbon.
Preferably, the palladium catalyst is palladium acetate, which is relatively inexpensive among a large number of palladium catalysts, and the reaction efficiency is high when palladium acetate is used as the catalyst.
As a further preference, the thioester compound containing an indolone structure is one of compounds shown in formula (I-1) and formula (I-5):
in the preparation method, the palladium acetate, the tricyclohexylphosphine and the cesium carbonate are generally commercially available products and can be conveniently obtained from the market.
Compared with the prior art, the invention has the beneficial effects that: the reaction raw materials are cheap and easy to obtain, the preparation method is simple, the operation is easy, the post-treatment is simple and convenient, the compatibility of substrate functional groups is strong, and the reaction efficiency is high. The method takes sulfonyl chloride compound as a sulfur source and carbonyl molybdenum as both a carbonyl source and a reducing agent, and provides a new way for constructing thioester compound containing indolone structure. Can synthesize a plurality of thioester compounds containing indolone structures according to actual needs, and has stronger practicability.
Detailed Description
The invention is further described with reference to specific examples.
Examples 1 to 15
Adding palladium acetate, tricyclohexylphosphine, molybdenum carbonyl, cesium carbonate, water, iodo-aromatic hydrocarbon (II) and sulfonyl chloride compound (III) into a 15mL sealed tube according to the raw material ratio of Table 1, then adding N, N-dimethylformamide (1 mL), uniformly mixing and stirring, reacting according to the reaction conditions of Table 2, filtering after the reaction is finished, mixing silica gel with a sample, and purifying by column chromatography to obtain a corresponding thioester compound (I) containing an indolone structure, wherein the reaction process is shown as the following formula:
TABLE 1 raw material addition amounts of examples 1 to 15
TABLE 2
In tables 1 and 2, T is the reaction temperature, T is the reaction time, me is methyl, bu is n-butyl, cy is cyclohexyl, CF 3 Is trifluoromethyl, iPr is isopropyl, tBu is tert-butyl, OMe is methoxy, ph is phenyl, et is ethyl, ts is p-toluenesulfonyl, and Bn is benzyl.
Structure confirmation data of the compounds prepared in examples 1 to 5:
nuclear magnetic resonance of thioester Compound (I-1) having an indolinone Structure obtained in example 1: ( 1 H NMR and 13 c NMR) the data were:
1 H NMR(400MHz,CDCl 3 )δ7.28–7.24(m,2H),7.12(d,J＝8.1Hz,2H),7.07–7.03(m,3H),6.82(d,J＝8.0Hz,1H),3.27(d,J＝16.0Hz,1H),3.25–3.19(m,4H),2.31(s,3H),1.40(s,3H).
13 C NMR(101MHz,CDCl 3 )δ193.9,179.3,143.4,139.7,134.3,132.2,129.9,128.1,123.6,122.8,122.3,108.2,49.7,46.2,26.4,24.1,21.3.
nuclear magnetic resonance of thioester Compound (I-2) having an indolinone Structure prepared in example 2: ( 1 H NMR and 13 c NMR) the data detected were:
1 H NMR(400MHz,CDCl 3 )δ7.27–7.22(m,2H),7.12(d,J＝8.1Hz,2H),7.06(d,J＝8.2Hz,2H),7.02(t,J＝7.5Hz,1H),6.83(d,J＝7.8Hz,1H),3.77–3.62(m,2H),3.25–3.16(m,2H),2.31(s,3H),1.69–1.62(m,2H),1.40–1.35(m,5H),0.93(t,J＝7.4Hz,3H).
13 C NMR(101MHz,CDCl 3 )δ193.7,179.1,142.8,139.6,134.3,132.4,129.9,128.0,123.9,123.1,122.0,108.5,49.6,46.2,39.9,29.4,24.2,21.2,20.1,13.7.
nuclear magnetic resonance of thioester Compound (I-3) having an indolinone Structure obtained in example 3: ( 1 H NMR and 13 c NMR) the data were:
1 H NMR(400MHz,CDCl 3 )δ7.27–7.24(m,1H),7.21–7.19(m,1H),7.03(td,J＝7.5,0.8Hz,1H),6.84(d,J＝7.8Hz,1H),3.33–3.27(m,1H),3.25(s,3H),3.16(d,J＝15.7Hz,1H),3.06(d,J＝15.7Hz,1H),1.75–1.54(m,4H),1.36(s,3H),1.33–1.15(m,6H).
13 C NMR(101MHz,CDCl 3 )δ195.0,179.6,143.4,132.3,128.0,122.7,122.2,108.1,50.4,46.2,42.2,32.8,32.6,26.4,25.71,25.70,25.4,24.1.
nuclear magnetic resonance of thioester Compound (I-4) having an indolinone Structure obtained in example 4: ( 1 H NMR and 13 c NMR) the data were:
1 H NMR(400MHz,CDCl 3 )δ7.54(d,J＝8.2Hz,1H),7.47(s,1H),7.13(d,J＝8.1Hz,2H),7.08(d,J＝8.2Hz,2H),6.87(d,J＝8.2Hz,1H),3.33(d,J＝16.4Hz,1H),3.27–3.23(m,4H),2.31(s,3H),1.41(s,3H).
13 C NMR(101MHz,CDCl 3 )δ194.0,179.3,146.5,140.0,134.4,132.9,130.1,126.0(q,J＝3.9Hz),124.5(q,J＝32.4Hz),124.4(q,J＝271.5Hz),123.3,119.7(q,J＝3.5Hz),108.0,49.5,46.0,26.6,24.1,21.3.
nuclear magnetic resonance of thioester Compound (I-5) having an indolinone Structure obtained in example 5: ( 1 H NMR and 13 c NMR) analysisThe measured data are as follows:
1 H NMR(400MHz,CDCl 3 )δ7.18(dd,J＝8.2,5.3Hz,1H),7.13(d,J＝8.0Hz,2H),7.08(d,J＝8.2Hz,2H),6.71(ddd,J＝10.3,8.3,2.3Hz,1H),6.55(dd,J＝8.9,2.3Hz,1H),3.26(d,J＝16.1Hz,1H),3.21–3.17(m,4H),2.31(s,3H),1.38(s,3H).
13 C NMR(101MHz,CDCl 3 )δ193.9,179.6,163.0(d,J＝244.6Hz),144.9(d,J＝11.6Hz),139.8,134.3,130.0,127.4(d,J＝2.8Hz),123.7(d,J＝9.8Hz),123.5,108.2(d,J＝22.4Hz),97.1(d,J＝27.6Hz),49.7,45.7,26.5,24.1,21.2。
Claims (9)
1. a preparation method of thioester compound containing indolone structure is characterized by comprising the following steps: reacting a palladium catalyst, a ligand, molybdenum carbonyl, alkali, water, iodo-aromatic hydrocarbon and a sulfonyl chloride compound at 90-110 ℃ for 20-28 hours, and after the reaction is completed, performing post-treatment to obtain the thioester compound containing the indolone structure;
the structure of the iodo-aromatic hydrocarbon is shown as the formula (II):
the sulfonyl chloride compound has a structure shown in a formula (III):
R 4 -SO 2 Cl (III)；
the structure of the thioester compound containing the indolone structure is shown as the formula (I):
in the formulae (I) to (III), R 1 Is H, C 1 ～C 4 Alkyl, trifluoromethylA group or a halogen;
R 2 is C 1 ～C 4 Alkyl or p-toluenesulfonyl;
R 3 is H or C 1 ～C 7 A hydrocarbyl group;
R 4 is C 1 ～C 6 Alkyl radical, C 1 ～C 6 Cycloalkyl, substituted or unsubstituted phenyl, the substituents on said phenyl being C 1 ～C 4 Alkyl, methoxy or phenyl.
2. The method for producing the thioester compound having an indolone structure according to claim 1, wherein R is 1 Is H, methyl, tert-butyl, trifluoromethyl, F or Br;
R 2 is methyl, ethyl, n-butyl or p-toluenesulfonyl;
R 3 is methyl or benzyl.
3. The method for producing the thioester compound having an indolone structure according to claim 1, wherein R is 4 Is cyclohexyl or substituted phenyl, and the substituent on the phenyl is methyl, isopropyl, tertiary butyl, methoxyl or phenyl.
4. The method for producing a thioester compound containing an indolinone structure according to claim 1, wherein the molar ratio of iodo aromatic hydrocarbon: sulfonyl chloride compound: molybdenum carbonyl: palladium catalyst: ligand: alkali: water = 1-1.5.
5. The method for producing a thioester compound containing an indolinone structure according to claim 1, wherein N, N-dimethylformamide is used as a solvent.
6. The method for preparing a thioester compound containing an indolone structure according to claim 1, wherein the palladium catalyst is palladium acetate.
7. The method for preparing a thioester compound containing an indolone structure according to claim 1, wherein the ligand is tricyclohexylphosphine.
8. The method for producing the thioester compound containing an indolone structure according to claim 1, wherein the base is cesium carbonate.
9. The method for preparing thioester compound containing an indolone structure according to claim 1, wherein the thioester compound containing an indolone structure is one of compounds represented by formula (I-1) to formula (I-5):
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