2-Bromo-1-(3,4-dimethoxyphenyl)ethan-1-one → Methyl 4-[4-(3,4-dimethoxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate

HRID 2298590Notes

Reaction equation

HRID 2298590 reaction equation
[NH2:1][C:2](=[S:13])[C:3]1[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=1[CH3:8].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:24](=O)[CH2:25]Br)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:24]2[N:1]=[C:2]([C:3]3[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=3[CH3:8])[S:13][CH:25]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Participants

3

Reactant 2

HCID 2704232-Bromo-1-(3,4-dimethoxyphenyl)ethan-1-oneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583813Methyl 4-[4-(3,4-dimethoxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylateYield 89.2%

Procedure

105 mg (0.424 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge Chemical Co. LTD., Cornwall, U.K.) was reacted with 1-(3,4-dimethoxyphenyl)-2-bromoethan-1-one (0.467 mmol; 120 mg) in a manner similar to Example 22, step (a) to afford 148 mg (85% yield) of methyl 4-[4-(3,4-dimethoxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate.

Sources & evidence

ORD record
ord-9fdc63c0c62f479c806dd07e88fb9516
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

Loading…