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

HRID 2186605Notes

Reaction equation

HRID 2186605 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].Br[CH2:24][C:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[Cl:33])=O>>[Cl:33][C:32]1[CH:31]=[CH:30][N:29]=[CH:28][C:27]=1[C:25]1[N:10]=[C:11]([C:12]2[CH:13]=[C:14]([C:18]([O:20][CH3:21])=[S:19])[S:15][C:16]=2[CH3:17])[S:22][CH:24]=1

Participants

4

Reactant 3

HCID 185374562-Bromo-1-(4-chloropyridin-3-yl)ethan-1-oneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylateHCID 1784259235-Methylthiothiophene-2-carboxylate

Product 1

HCID 86758180Methyl 4-[4-(4-chloro(3-pyridyl))(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylateYield 80.4%

Procedure

Methyl 4-4-(4-chloro(3-pyridyl))(3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate: 240 mg (0.970 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge Chemical Co. LTD., Cornwall, U.K.) was reacted with 2-bromo-1-(4-chloro(3-pyridyl))ethan-1-one (1.06 mmol; 250 mg) in a manner similar to Example 22, step (a) to afford 286 mg (77% yield) of methyl 4-[4-(4-chloro(3-pyridyl))(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate.

Sources & evidence

ORD record
ord-74684349609842b6b455d4a2bd75d9e9
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

Loading…