Thioacetamide → 2-methyl-5,6-dihydro-4H-thiazolo[4,5-e]indole-8-carboxylic acid ethyl ester

HRID 481088Notes

Reaction equation

HRID 481088 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:13](=O)[CH:12](Br)[CH2:11][CH2:10][C:9]=2[N:8](C(OC(C)(C)C)=O)[CH:7]=1)=[O:5])[CH3:2].[C:24]([NH2:27])(=[S:26])[CH3:25]>CO>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:13]3[N:27]=[C:24]([CH3:25])[S:26][C:12]=3[CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 208723925-Bromo-4-oxo-4,5,6,7-tetrahydro-indole 1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Product 1

HCID 206056232-methyl-5,6-dihydro-4H-thiazolo[4,5-e]indole-8-carboxylic acid ethyl esterYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-4-oxo-4,5,6,7-tetrahydro-indole 1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (0.78 mmol) in 10 mL CH3OH is added thioacetamide (1.55 mmol). After stirring under refluxing for 16 hours the solvent is removed in vacuo. The brown oil is chromatographed using EtOAc 1: hexane 1, followed by 5% MeOH in CH2Cl2 as mobile phases to yield 2-methyl-5,6-dihydro-4H-thiazolo[4,5-e]indole-8-carboxylic acid ethyl ester as a white solid (34%). 1H NMR (DMSO-d6) 1.27 (t, 3H), 2.60 (s, 3H), 2.78(t, 2H), 2.96 (t, 2H), 4.19 (q, 2H), 7.21 (s, 1H), 11.44 (s, 1H).

Workup

  1. temperatureunder refluxing for 16 hours the solvent
  2. customis removed in vacuo
  3. customThe brown oil is chromatographed

Sources & evidence

ORD record
ord-0b40637a84394d2fa4e8e704a97366a3
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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