GB1167777A - Indole Derivatives - Google Patents

Indole Derivatives

Info

Publication number
GB1167777A
GB1167777A GB3763967A GB3763967A GB1167777A GB 1167777 A GB1167777 A GB 1167777A GB 3763967 A GB3763967 A GB 3763967A GB 3763967 A GB3763967 A GB 3763967A GB 1167777 A GB1167777 A GB 1167777A
Authority
GB
United Kingdom
Prior art keywords
methyl
chlorobenzoyl
malonate
chlorine
butyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB3763967A
Inventor
John Martin Chemerda
Meyer Sletzinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1167777A publication Critical patent/GB1167777A/en
Expired legal-status Critical Current

Links

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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
    • C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,167,777. lndole derivatives. MEROK & CO. Inc. 16 Aug., 1967 [23 Aug., 1966], No. 37639/67. Heading C2C. Novel indole derivatives of the general formula wherein X is a chlorine or bromine atom or a p-toluene-sulphonyloxy group and X<SP>1</SP> is a hydrogen, chlorine or bromine atom are prepared (a) when X is a chlorine or bromine atom and X<SP>1</SP> is a hydrogen atom, by refluxing di-t-butyl 1-p - chlorobenzoyl - 2 - methyl - 5 - methoxyindole- 3-α-(bromo or chloro)malonate in a solvent until evolution of isobutylene ceases; (b) when X and X<SP>1</SP> are each a chlorine or bromine atom, by refluxing the malonate specified in (a) above in toluene in the presence of p-toluenesulphonic acid until one equivalent of isobutylene is collected, halogenating the resulting t-butyl 1- p - chlorobenzoyl - 2 - methyl - 5 - methoxy - indole- 3-α-(bromo or chloro)acetate with an ethereal solution of chlorine or bromine and heating the resulting t-butyl 1-p-chlorobenzoyl-2-methyl- 5 - methoxyindole - 3 - α α - di - (bromo or chloro)- acetate with p-toluenesulphonic acid in toluene; or (c) when X is a p-toluenesulphonyloxy group and X<SP>1</SP> is a hydrogen atom, by treatment of the malonate specified in (a) above with silver nitrate in aqueous acetone, followed by treatment of the resulting 1.p.chlorobenzoyl-2.methyl-5- methoxy-indole-3-α-hydroxyacetic acid with ptoluenesulphonylchloride. Di - t - butyl 1 - p - chlorobenzoyl - 2 - methyl- 5 - methoxyindole - 3 - α - (bromo or chloro)- malonate is prepared by condensing p-methoxyphenylhydrazine with 2-acetonylmalonic acid di-t-butyl ester, treating the resulting di-tbutyl 2 - methyl - 5 - methoxyindole - 3 - malonate with p-chlorobenzoyl chloride and sodium hydride and treating the resulting di-t-butyl 1 - p - chlorobenzoyl - 2 - methyl - 5 - methoxyindole- 3-malonate with bromine or chlorine in a solvent. Indole derivatives of the above general formula may be reduced to give 1 -p-chlorobenzoyl - 2 - methyl - 5 - methoxy - 3 - indolylacetic acid, e.g. by means of hydrogen in the presence of a noble metal or Raney nickel catalyst, or hydrogen generated in situ.
GB3763967A 1966-08-23 1967-08-16 Indole Derivatives Expired GB1167777A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA968566 1966-08-23

Publications (1)

Publication Number Publication Date
GB1167777A true GB1167777A (en) 1969-10-22

Family

ID=4142636

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3763967A Expired GB1167777A (en) 1966-08-23 1967-08-16 Indole Derivatives

Country Status (4)

Country Link
CH (1) CH505822A (en)
DE (1) DE1695452A1 (en)
GB (1) GB1167777A (en)
NL (1) NL6711390A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0143424A2 (en) 1983-11-25 1985-06-05 Fuji Photo Film Co., Ltd. Heat-developable light-sensitive materials
EP0210660A2 (en) 1985-07-31 1987-02-04 Fuji Photo Film Co., Ltd. Image forming process
EP0772088A1 (en) 1991-03-05 1997-05-07 Fuji Photo Film Co., Ltd. Heat-developable diffusion transfer color photographic material

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0143424A2 (en) 1983-11-25 1985-06-05 Fuji Photo Film Co., Ltd. Heat-developable light-sensitive materials
EP0210660A2 (en) 1985-07-31 1987-02-04 Fuji Photo Film Co., Ltd. Image forming process
EP0772088A1 (en) 1991-03-05 1997-05-07 Fuji Photo Film Co., Ltd. Heat-developable diffusion transfer color photographic material

Also Published As

Publication number Publication date
NL6711390A (en) 1968-02-26
CH505822A (en) 1971-04-15
DE1695452A1 (en) 1971-07-08

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee