Ethyl 3-chloro-2-oxopentanoate → 2-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-5-ethyl-thiazole-4-carboxylic acid ethyl ester

HRID 644041Notes

Reaction equation

HRID 644041 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19](=[S:21])[NH2:20])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:22]([O:24][C:25](=[O:32])[C:26](=O)[CH:27](Cl)[CH2:28][CH3:29])[CH3:23]>CN(C)C=O>[CH2:22]([O:24][C:25]([C:26]1[N:20]=[C:19]([C:10]2[C:11]3[C:16](=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:9]=2)[S:21][C:27]=1[CH2:28][CH3:29])=[O:32])[CH3:23]

Participants

4

Reactant 2

HCID 13719444Ethyl 3-chloro-2-oxopentanoateHCID 86073268HCID 86073268, compound

Product 1

HCID 686949202-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-5-ethyl-thiazole-4-carboxylic acid ethyl esterYield 152.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbothioic acid amide (0.227 g, 0.754 mmol) and crude 3-chloro-2-oxo-pentanoic acid ethyl ester (1.34 g, 7.52 mmol) in dimethylformamide (4 ml) was subjected to microwave irradiation for 25 min at 140° C. The reaction mixture was concentrated in vacuo and the obtained reside was purified by silica gel column chromatography eluting with 25% acetone in heptane to afford crude 2-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-5-ethyl-thiazole-4-carboxylic acid ethyl ester (0.490 g). This material was used in the next step without further purification.

Workup

  1. customirradiation for 25 min at 140° C
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe obtained reside was purified by silica gel column chromatography
  4. washeluting with 25% acetone in heptane

Sources & evidence

ORD record
ord-afc903a5336744a697ca743d7acd9aec
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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