Trichloroacetyl chloride → 2,2,2-Trichloro-N-(2-methyl-thieno[2,3-c]pyridin-3-yl)-acetamide

Participants

Reaction Conditions

Reaction Steps

Methyl-3-nitro-thieno[2,3-c]pyridine (2.05 g, 10.6 mmol) was dissolved in MeOH (250 mL) and added to a suspension of Raney-Nickel (20 g) in MeOH (100 mL). The reaction flask was flushed with H2. After 3 hours at room temperature under a balloon of H2 the reaction mixture was filtered and condensed to provide a yellow solid. This was then dissolved in DCM (100 mL) and triethylamine (1.6 mL, 11.5 mmol) was added. The solution was cooled to 0° C. in an ice bath. Trichloroacetyl chloride (1.3 mL, 11.6 mmol) was added dropwise. The solution was allowed to slowly warm to room temperature and stirred overnight (16 hrs), then concentrated to a yellow paste and partitioned between equal volumes of water and EtOAc (150 mL each). After separation the organic phase was washed with water (2×70 mL) and brine (1×70 mL), dried (MgSO4) and condensed to provide the title compound as a tan solid (1.63 g, 42%). Used without purification.

Provenance & Evidence