Propanethioamide → 2-Ethyl-5,6-dihydro-4H-thiazolo[4,5-e]indole-8-carboxylic Acid Ethyl Ester

HRID 481089Notes

Reaction equation

HRID 481089 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]([NH2:28])(=[S:27])[CH2:25][CH3:26]>>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:13]3[N:28]=[C:24]([CH2:25][CH3:26])[S:27][C:12]=3[CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 2760628PropanethioamideHCID 208723925-Bromo-4-oxo-4,5,6,7-tetrahydro-indole 1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Product 1

HCID 206056052-Ethyl-5,6-dihydro-4H-thiazolo[4,5-e]indole-8-carboxylic Acid Ethyl Ester

Procedure

The title compound is prepared by reacting 5-bromo-4-oxo-4,5,6,7-tetrahydro-indole 1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester with thiopropionamide essentially according to the procedures described in Example 15, Step 3. 1H NMR (CDCl3) 1.33-1.42 (m, 6H), 2.80-2.90 (m, 2H), 2.98-3.10 (m, 4H), 2.37 (q, 2H), 7.24 (s, 1H), 8.60 (s, 1H).

Sources & evidence

ORD record
ord-357056cc882640b6872bb5a6dd2f0ad5
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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