Potassium Carbonate → HCID 69586224, compound

Participants

Reaction Steps

A solution of 4-(7-chloro-1H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester ((from above step c) 0.201 g, 0.499 mmol) in DMF (4 mL) was treated with α-bromo-2,6-difluorotoluene (0.114 g, 0.549 mmol) and solid K2CO3 (0.152 g, 1.10 mmol). The reaction was stirred at room temperature 17 h, diluted with EtOAc and washed well with water (5×150 mL). The organic layer was dried over MgSO4 and concentrated in vacuo. Silica gel chromatography (2% MeOH with 2 M NH3 in CH2Cl2) afforded the products 4-[7-chloro-3-(2,6-difluoro-benzyl)-3H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester and 4-[7-chloro-1-(2,6-difluoro-benzyl)-1H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester (0.102 g, 38%). These isomers were not separable by silica gel chromatography, but they were carried on together into the next reaction.

Provenance & Evidence