CN104356053A - Preparation method of 2-(3-halogen phenyl) pyridine derivative - Google Patents

Preparation method of 2-(3-halogen phenyl) pyridine derivative Download PDF

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CN104356053A
CN104356053A CN201410563504.4A CN201410563504A CN104356053A CN 104356053 A CN104356053 A CN 104356053A CN 201410563504 A CN201410563504 A CN 201410563504A CN 104356053 A CN104356053 A CN 104356053A
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pyridine
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phenylpyridine
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CN104356053B (en
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黄剑辉
于庆贞
胡乐安
王悦
赵康
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Tianjin University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms

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Abstract

The invention discloses a preparation method of a 2-(3-halogen phenyl) pyridine derivative. The preparation method comprises the following steps: dissolving 2-phenylpyridine or substitutive 2-phenylpyridine (I) and N-halogenated butyl diimide (II) into a solvent, adding a ruthenium catalyst for reaction at the temperature of 70-150 DEG C for 24-48 hours to obtain a mixture, extracting with ethyl acetate, separating and purifying the mixture by column chromatography after the mixture is washed and dried to obtain the 2-(3-halogen phenyl) pyridine derivative (III), wherein the reaction formula of the 2-(3-halogen phenyl) pyridine derivative is shown in the specification. The preparation method has the advantages of simplicity in operation, higher yield and the like; furthermore, reaction raw materials and reaction reagents are readily available, and multiple types of product substitutes are produced.

Description

The preparation method of 2-(3-halogen phenyl) pyridine derivatives
Technical field
The present invention relates to the preparation method of 2-(3-halogen phenyl) pyridine derivatives.
Background technology
Aryl halide is the important chemical intermediate of a class, and it can introduce different functional groups by transition metal-catalyzed coupling, synthesizes comparatively complex compound, as natural compounds or the medicine of some complexity.The method of the introducing halogen of classics mainly contained the nucleophilic substitution reaction of aromatic ring and the halogenating reaction of transistion metal compound intermediate in the past.They can only introduce halogen in the adjacency pair position of supplied for electronic.The phenyl ring that electron-withdrawing group replaces, due to the passivation of electron withdrawing group, the example introducing halogen in a position is considerably less.Therefore, exploitation one can high regioselectivity, and the method introducing aromatic ring halogen in a position very has meaning.
As a kind of supplementary aryl halogenation strategy, transition metal-catalyzed face position guiding and the introducing halogen of highly selective has developed into a kind of new effective ways.At present, the metal being applied to this field comprises palladium, gold, ruthenium, rhodium and copper.It is emphasized that pyridyl is proved to be more effectively to lead one of base in transition metal-catalyzed facing in a halogenating reaction.
Recently, Frost and Ackermann reports position between the catalysis of transition metal ruthenium respectively and optionally builds carbon-sulfur bond and carbon-carbon bond.But they do not realize the structure of carbon-halogen bond.
[1]A.F.Littke,G.C.Fu,Angew.Chem.2002,114,4350-4386；Angew.Chem.Int.Ed.2002,41,4176-4211；
[2]P.B.De la Mare,Electrophilic halogenation,Cambridge University Press,Cambridge,1976,chap.5.
[3]V.Snieckus,Chem.Rev.1990,90,879–933.
[4]D.Kalyani,A.R.Dick,W.Q.Anani,M.S.Sanford,Org.Lett.2006,8,2523–2526.
[5]A.R.Dick,K.L.Hull,M.S.Sanford,J.Am.Chem.Soc.2004,126,2300-2301；
[6]F.Y.Mo,J.M.Yan,D.Qiu,F.Li,Y.Zhang,J.B.Wang,Angew.Chem.Int.Ed.2010,49,2028–2032.
[7]N. J.Wencel-Delord,F.Glorius,J.Am.Chem.Soc.2012,134,8298–8301.
[8]L.H.Wang,L.Ackermann,Chem.Commun.2014,1083-1085.
[9]L.Menini,E.V.Gusevskaya,Chem.Commun.2006,209–211
But the method being introduced aryl halogen synthesis 2-(3-halogen phenyl) pyridine derivatives by position selectivity between the catalysis of transition metal ruthenium is not also reported.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, the preparation method of a kind of 2-(3-halogen phenyl) pyridine derivatives is provided.
Technical scheme of the present invention is summarized as follows:
The preparation method of 2-(3-halogen phenyl) pyridine derivatives, comprise the steps: 2-phenylpyridine or replace 2-phenylpyridine (I), N-N-halosuccinimides (II) is dissolved in solvent, add ruthenium catalyst in 70-150 DEG C of reaction 24-48 hour, be extracted with ethyl acetate, through column chromatography separating purification after washing, drying, obtain 2-(3-halogen phenyl) pyridine derivatives (III); Its reaction formula is:
Wherein R 1for hydrogen, fluorine, chlorine, bromine, methyl, benzyl, sec.-propyl, the tertiary butyl, phenyl or methoxyl group;
R 2for hydrogen, fluorine, chlorine, bromine, iodine, methyl, methoxyl group, vinyl, oxyethyl group formyl ester group or trifluoromethyl;
X is chlorine, bromine or iodine;
Ruthenium catalyst is divalent ruthenium catalyzer or trivalent ruthenium catalyst.
Replace 2-phenylpyridine (I) and be preferably 2-(4-aminomethyl phenyl) pyridine, 2-(4-p-methoxy-phenyl) pyridine, 2-(2-p-methoxy-phenyl) pyridine, 2-(2-aminomethyl phenyl) pyridine, 2-(4-fluorophenyl) pyridine, 2-(4-chloro-phenyl-) pyridine, 2-(4-bromophenyl) pyridine, 2-(4-iodophenyl) pyridine, 2-(4-ethenylphenyl) pyridine, 2-(4-oxyethyl group formylphenyl) pyridine, 2-(4-trifluoromethyl) pyridine, 2-phenyl-4-methvl-pyridinium, 2-phenyl-4-benzyl-pyridine, 2-phenyl-4-sec.-propyl-pyridine, 2-phenyl-4-tert-Butyl-pyridin, 2-phenyl-4-methoxv-pyridine, the fluoro-pyridine of 2-phenyl-4-, the chloro-pyridine of 2-phenyl-4-, the bromo-pyridine of 2-phenyl-4-, 2-phenyl-3-methvl-pyridinium, 2-phenyl-4-phenyl-pyridin.
Ruthenium catalyst is preferably (4-cymene) ruthenous chloride dimer, (1,5-cyclooctadiene) ruthenous chloride, Ge Labu catalyzer, (1.2.3.4.5-pentamethylcyclopentadiene) ruthenous chloride polymer, ruthenium trichloride.
Solvent is estimated and is elected N,N-dimethylacetamide as, DMF, N-Methyl pyrrolidone, Isosorbide-5-Nitrae-dioxane, acetonitrile or ethylene dichloride.
The present invention has simple to operate, and reaction raw materials and reaction reagent are easy to get, and product substituting group type is various, and yield is advantages of higher comparatively.
Embodiment
The synthetic method reaction equation of 2-of the present invention (3-halogen phenyl) pyridine derivatives (III) is:
Reaction raw materials 2-phenylpyridine (I) required in each embodiment is reference literature method preparation (A.Khalafi-Nezhad, F.Panahi, Green Chem.2011,13,2408 – 2415.)
Below in conjunction with specific embodiment, the present invention is further illustrated.
Embodiment 1
The preparation of 2-(3-bromophenyl) pyridine (III-a):
By 2-phenylpyridine (I-a) (47mg, 0.3mmol), N-bromo-succinimide (II) (108mg, 0.6mmol), be dissolved in N, N-N,N-DIMETHYLACETAMIDE (0.2M, 1.5mL), add (4-cymene) ruthenous chloride dimer (9mg, 5mol%), react 24 hours at 70 DEG C, add ethyl acetate (20mL) extraction, wash with water (10mLx3), organic phase is filtered after anhydrous sodium sulfate drying, revolve and desolventize, crude product is through column chromatography separating purification, obtain 2-(3-bromophenyl) pyridine (III-a) 61mg, for colorless oil, productive rate: 87%. 1H NMR(600MHz,CDCl 3):δ8.70(t,J＝4.8,1H),8.17(t,J＝1.6,1H),7.91(d,J＝7.8,1H),7.77(td,J＝7.8,1.7,1H),7.71(d,J＝7.9,1H),7.54(dd,J＝7.9,0.9,1H),7.35(t,J＝7.9,1H),7.30–7.25(m,1H). 13C NMR(151MHz,CDCl 3)δ154.86,148.79,140.40,135.90,130.85,129.23,129.02,124.39,122.04,121.66,119.59.
Substitute the N-bromo-succinimide of the present embodiment with N-chlorosuccinimide, other same the present embodiment, experiment proves, prepares 2-(3-chloro-phenyl-) pyridine; Substitute the N-bromo-succinimide of the present embodiment with N-N-iodosuccinimide, other same the present embodiment, experiment proves, prepares 2-(3-iodophenyl) pyridine.
Embodiment 2
The preparation of (the bromo-4-p-methoxy-phenyl of 3-) pyridine (III-b):
By 2-(4-p-methoxy-phenyl) pyridine (I-b) (56mg, 0.3mmol), N-bromo-succinimide (II) (108mg, 0.6mmol), be dissolved in N, dinethylformamide (0.2M, 1.5mL), add (1, 5-cyclooctadiene) ruthenous chloride (8mg, 10mol%), react 24 hours at 150 DEG C, add ethyl acetate (20mL) extraction, wash with water (10mLx3), organic phase is filtered after anhydrous sodium sulfate drying, revolve and desolventize, crude product is through column chromatography separating purification, obtain (the bromo-4-p-methoxy-phenyl of 3-) pyridine (III-b) 72mg, for colorless oil, productive rate: 90%. 1H NMR(600MHz,CDCl 3)δ8.66(d,J＝4.6Hz,1H),8.23(d,J＝2.1Hz,1H),7.93(dd,J＝8.6,2.0Hz,1H),7.73(t,J＝7.5Hz,1H),7.65(d,J＝7.9Hz,1H),7.20(t,J＝6.0Hz,1H),6.99(d,J＝8.6Hz,1H),3.95(s,3H). 13C NMR(151MHz,CDCl 3)δ156.56,155.68,149.65,136.84,133.30,131.85,127.01,121.95,119.87,112.14,111.83,56.36.
Embodiment 3
The preparation of 2-(the bromo-4-aminomethyl phenyl of 3-) pyridine (III-c):
By 2-(4-aminomethyl phenyl) pyridine (I-c) (51mg, 0.3mmol), N-bromo-succinimide (II) (108mg, 0.6mmol), be dissolved in N-Methyl pyrrolidone (0.2M, 1.5mL), add the granny rag catalyzer (10mol%) that accords with regular rules, react 48 hours at 100 DEG C, add ethyl acetate (20mL) extraction, wash with water (10mLx3), organic phase is filtered after anhydrous sodium sulfate drying, revolve and desolventize, crude product is through column chromatography separating purification, obtain 2-(the bromo-4-aminomethyl phenyl of 3-) pyridine (III-c) 67mg, for colorless oil, productive rate: 89%. 1H NMR(600MHz,CDCl 3)δ8.61(d,J＝4.4Hz,1H),8.13(s,1H),7.75(dd,J＝7.9,1.4Hz,1H),7.67(tt,J＝9.1,4.6Hz,1H),7.62(d,J＝7.8Hz,1H),7.25(d,J＝7.9Hz,1H),7.16(t,J＝6.6Hz,1H),2.38(s,3H). 13C NMR(151MHz,CDCl 3)δ155.87,149.73,138.77,138.64,136.86,131.05,130.71,125.58,125.48,122.38,120.33,22.77.
Embodiment 4
The preparation of 2-(the bromo-4-chloro-phenyl-of 3-) pyridine (III-d)
By 2-(4-chloro-phenyl-) pyridine (I-d) (57mg, 0.3mmol), N-bromo-succinimide (II) (108mg, 0.6mmol), be dissolved in ethylene dichloride (0.2M, 1.5mL), add (1.2.3.4.5-pentamethylcyclopentadiene) ruthenous chloride polymer (5mol%), react 24 hours at 120 DEG C, add ethyl acetate (20mL) extraction, wash with water (10mLx3), organic phase is filtered after anhydrous sodium sulfate drying, revolve and desolventize, crude product is through column chromatography separating purification, obtain 2-(the bromo-4-chloro-phenyl-of 3-) pyridine (III-d) 58mg, for white solid, productive rate: 72%. 1H NMR(600MHz,CDCl 3)δ8.69(d,J＝4.6Hz,1H),8.30(d,J＝2.0Hz,1H),7.86(dt,J＝19.9,10.0Hz,1H),7.77(td,J＝7.8,1.6Hz,1H),7.69(d,J＝7.9Hz,1H),7.54(d,J＝8.4Hz,1H),7.32–7.22(m,1H). 13C NMR(151MHz,CDCl 3)δ154.81,149.87,139.35,137.02,135.09,132.08,130.52,126.66,122.99,122.87,120.40.
With 2-(4-fluorophenyl) pyridine (I-h), 2-(4-bromophenyl) pyridine (I-i), 2-(4-iodophenyl) pyridine (I-j), 2-(4-ethenylphenyl) pyridine (I-k), 2-(4-oxyethyl group formylphenyl) pyridine (I-l) or 2-(4-trifluoromethyl) pyridine (I-m) substitute 2-(4-chloro-phenyl-) pyridine (I-d) of the present embodiment respectively, other same the present embodiment, experiment proves, prepare 2-(the bromo-4-fluorophenyl of 3-) pyridine (III-h), 2-(the bromo-4-bromophenyl of 3-) pyridine (III-i), 2-(the bromo-4-iodophenyl of 3-) pyridine (III-j), 2-(the bromo-4-ethenylphenyl of 3-) pyridine (III-k), 2-(3-bromo-4-oxyethyl group formylphenyl) pyridine (III-l) or 2-(the bromo-4-trifluoromethyl of 3-) pyridine (III-m).
Embodiment 5
The preparation of 2-(the bromo-2-p-methoxy-phenyl of 3-) pyridine (III-e)
By 2-(2-p-methoxy-phenyl) pyridine (I-e) (56mg, 0.3mmol), N-bromo-succinimide (II) (108mg, 0.6mmol), be dissolved in acetonitrile (0.2M, 1.5mL), add (1, 5-cyclooctadiene) ruthenous chloride (8mg, 10mol%), react 24 hours at 80 DEG C, add ethyl acetate (20mL) extraction, wash with water (10mLx3), organic phase is filtered after anhydrous sodium sulfate drying, revolve and desolventize, crude product is through column chromatography separating purification, obtain 2-(the bromo-2-p-methoxy-phenyl of 3-) pyridine (III-e) 70mg, for colorless oil, productive rate: 88%. 1H NMR(600MHz,CDCl 3)δ8.71(d,J＝4.2Hz,1H),7.92(d,J＝2.6Hz,1H),7.80(d,J＝8.7Hz,1H),7.70(td,J＝7.8,1.7Hz,1H),7.48–7.41(m,1H),7.25–7.19(m,1H),6.87(d,J＝8.8Hz,1H),3.83(s,3H). 13C NMR(151MHz,CDCl 3)δ156.09,154.57,149.51,135.83,133.72,132.43,130.87,125.10,122.18,113.49,113.18,55.89.
Embodiment 6
The preparation of 2-(the bromo-2-aminomethyl phenyl of 3-) pyridine (III-f)
By 2-(o-tolyl) pyridine (I-f) (51mg, 0.3mmol), N-bromo-succinimide (II) (108mg, 0.6mmol), be dissolved in 1, 4-dioxane (0.2M, 1.5mL), add Grubbs catalyzer (10mol%), react 48 hours at 100 DEG C, add ethyl acetate (20mL) extraction, wash with water (10mLx3), organic phase is filtered after anhydrous sodium sulfate drying, revolve and desolventize, crude product is through column chromatography separating purification, obtain 2-(the bromo-2-aminomethyl phenyl of 3-) pyridine (III-f) 50mg, for colorless oil, productive rate: 67%. 1H NMR(600MHz,CDCl 3)δ8.70(d,J＝4.4Hz,1H),7.76(td,J＝7.7,1.6Hz,1H),7.61(d,J＝7.9Hz,1H),7.36(d,J＝7.8Hz,1H),7.33–7.26(m,2H),7.13(t,J＝7.8Hz,1H),2.37(s,3H). 13C NMR(151MHz,CDCl 3)δ159.60,149.32,142.57,136.31,135.70,132.57,128.85,126.94,126.51,124.22,122.09,20.64.
Embodiment 7
The preparation of 2-(3-bromophenyl)-4-picoline (III-g)
By 2-phenyl-4-picoline (I-g) (51mg, 0.3mmol), N-bromo-succinimide (II) (108mg, 0.6mmol), be dissolved in acetonitrile (0.2M, 1.5mL), add ruthenium trichloride (10mol%), react 24 hours at 120 DEG C, add ethyl acetate (20mL) extraction, wash with water (10mLx3), organic phase is filtered after anhydrous sodium sulfate drying, revolve and desolventize, crude product is through column chromatography separating purification, obtain 2-(3-bromophenyl)-4-picoline (III-g) 73mg, for colorless oil, productive rate: 85%. 1H NMR(400MHz,CDCl 3)δ8.47(d,J＝5.0Hz,1H),8.07(t,J＝1.7Hz,1H),7.82(d,J＝7.8Hz,1H),7.49–7.41(m,2H),7.25(t,J＝7.9Hz,1H),7.01(d,J＝7.5Hz,1H),2.34(s,3H). 13C NMR(151MHz,CDCl 3)δ154.73,148.50,146.98,140.53,130.69,129.16,129.00,124.41,122.66,121.95,120.56,20.20.
With 2-phenyl-4-benzyl-pyridine (I-n), 2-phenyl-4-sec.-propyl-pyridine (I-o), 2-phenyl-4-tert-Butyl-pyridin (I-p), 2-phenyl-4-methoxv-pyridine (I-q), the fluoro-pyridine of 2-phenyl-4-(I-r), the chloro-pyridine of 2-phenyl-4-(I-s), the bromo-pyridine of 2-phenyl-4-(I-t), 2-phenyl-3-methvl-pyridinium (I-u) or 2-phenyl-4-phenyl-pyridin (I-v) substitutes 2-phenyl-4-methvl-pyridinium (I-g) of the present embodiment respectively, other same the present embodiment, experiment proves, prepare 2-(3-bromophenyl)-4-benzyl-pyridine (III-n), 2-(3-bromophenyl)-4-sec.-propyl-pyridine (III-o), 2-(3-bromophenyl)-4-tert-Butyl-pyridin (III-p), 2-(3-bromophenyl)-4-methoxv-pyridine (III-q), the 2-fluoro-pyridine of (3-bromophenyl)-4-(III-r), the 2-chloro-pyridine of (3-bromophenyl)-4-(III-s), the 2-bromo-pyridine of (3-bromophenyl)-4-(III-t), 2-(3-bromophenyl)-3-methvl-pyridinium (III-u) or 2-(3-bromophenyl)-4-phenyl-pyridin (III-v).
The above; be only section Example of the present invention, not any pro forma restriction done to the present invention, every any simple amendment above-described embodiment done according to technical spirit of the present invention; equivalent variations and modification, all belong to protection scope of the present invention.

Claims (4)

  1. The preparation method of 1.2-(3-halogen phenyl) pyridine derivatives, it is characterized in that comprising the steps: 2-phenylpyridine or replacing 2-phenylpyridine (I), N-N-halosuccinimides (II) is dissolved in solvent, add ruthenium catalyst in 70-150 DEG C of reaction 24-48 hour, be extracted with ethyl acetate, through column chromatography separating purification after washing, drying, obtain 2-(3-halogen phenyl) pyridine derivatives (III); Its reaction formula is:
    Wherein R 1for hydrogen, fluorine, chlorine, bromine, methyl, benzyl, sec.-propyl, the tertiary butyl, phenyl or methoxyl group;
    R 2for hydrogen, fluorine, chlorine, bromine, iodine, methyl, methoxyl group, vinyl, oxyethyl group formyl ester group or trifluoromethyl;
    X is chlorine, bromine or iodine;
    Ruthenium catalyst is divalent ruthenium catalyzer or trivalent ruthenium catalyst.
  2. 2. preparation method according to claim 1, it is characterized in that described replacement 2-phenylpyridine (I) is for 2-(4-aminomethyl phenyl) pyridine, 2-(4-p-methoxy-phenyl) pyridine, 2-(2-p-methoxy-phenyl) pyridine, 2-(2-aminomethyl phenyl) pyridine, 2-(4-fluorophenyl) pyridine, 2-(4-chloro-phenyl-) pyridine, 2-(4-bromophenyl) pyridine, 2-(4-iodophenyl) pyridine, 2-(4-ethenylphenyl) pyridine, 2-(4-oxyethyl group formylphenyl) pyridine, 2-(4-trifluoromethyl) pyridine, 2-phenyl-4-methvl-pyridinium, 2-phenyl-4-benzyl-pyridine, 2-phenyl-4-sec.-propyl-pyridine, 2-phenyl-4-tert-Butyl-pyridin, 2-phenyl-4-methoxv-pyridine, the fluoro-pyridine of 2-phenyl-4-, the chloro-pyridine of 2-phenyl-4-, the bromo-pyridine of 2-phenyl-4-, 2-phenyl-3-methvl-pyridinium, 2-phenyl-4-phenyl-pyridin.
  3. 3. method according to claim 1, it is characterized in that described ruthenium catalyst is (4-cymene) ruthenous chloride dimer, (1,5-cyclooctadiene) ruthenous chloride, lattice granny rag catalyzer, (1.2.3.4.5-pentamethylcyclopentadiene) ruthenous chloride polymer, ruthenium trichloride.
  4. 4. preparation method according to claim 1, is characterized in that described solvent is N,N-dimethylacetamide, DMF, N-Methyl pyrrolidone, Isosorbide-5-Nitrae-dioxane, acetonitrile or ethylene dichloride.
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