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 2186606Notes

Reaction equation

HRID 2186606 reaction equation
CC1SC(C([O-])=S)=CC=1.[NH2:10][C:11](=[S:22])[C:12]1[CH:13]=[C:14]([C:18]([O:20][CH3:21])=[S:19])[S:15][C:16]=1[CH3:17].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:33](=O)[CH2:34]Br)[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]>>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:33]2[N:10]=[C:11]([C:12]3[CH:13]=[C:14]([C:18]([O:20][CH3:21])=[S:19])[S:15][C:16]=3[CH3:17])[S:22][CH:34]=2)[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]

Participants

4

Reactant 3

HCID 2704232-Bromo-1-(3,4-dimethoxyphenyl)ethan-1-oneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylateHCID 1784259235-Methylthiothiophene-2-carboxylate

Product 1

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

Procedure

Methyl 4-4-(3,4-dimetioxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate: 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-86316df6a0dc46a7b78e5a049ad50029
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

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