1-Acetoxy-2-bromoethane → 2-[2-(4'-Chloro-4-methoxy-biphenyl-2-yl)-quinolin-6-yl]-3-cyclohexyl-1-methoxycarbonylmethyl-1H-indole-6-carboxylic acid methyl ester

HRID 39050

Reaktionsgleichung

Reaktionsgleichung von HRID 39050
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)=[C:10]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[C:19]([C:24]3[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=3[C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[CH:18]=[CH:17]4)[NH:11]2)=[CH:7][CH:6]=1)=[O:4].BrC[CH2:47][O:48][C:49](=[O:51])[CH3:50].[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)=[C:10]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[C:19]([C:24]3[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=3[C:32]3[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=3)[CH:18]=[CH:17]4)[N:11]2[CH2:50][C:49]([O:48][CH3:47])=[O:51])=[CH:7][CH:6]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 587102282-[2-(4'-Chloro-4-methoxy-biphenyl-2-yl)-quinolin-6-yl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

Produkt 1

HCID 595490422-[2-(4'-Chloro-4-methoxy-biphenyl-2-yl)-quinolin-6-yl]-3-cyclohexyl-1-methoxycarbonylmethyl-1H-indole-6-carboxylic acid methyl esterAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of intermediate 15-2 (1.024 g, 1.7 mmol) and bromoethylacetate (388 mg, 1.5 eq) in dry DMF (30 mL) was added NaH (60% dispersion in mineral oil, 122 mg, 1.8 eq) at 0° C. After stirring for 20 min at this temperature, the reaction mixture was warmed up to room temperature. After 24 h, the reaction mixture was poured into 300 mL of ice-cold water. The formed yellow solid was filtered off, washed with petroleum ether and purified by column chromatography (CH2Cl2) to give 450 mg (39%) of 2-[2-(4′-Chloro-4-methoxy-biphenyl-2-yl)-quinolin-6-yl]-3-cyclohexyl-1-methoxycarbonylmethyl-1H-indole-6-carboxylic acid methyl ester 15-3; m/z=674 (M+H+).

Aufarbeitung

  1. waitAfter 24 h
  2. filtrationThe formed yellow solid was filtered off
  3. washwashed with petroleum ether
  4. custompurified by column chromatography (CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e3e2d91086f047599e295103f0017a3d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524716B2

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