Methyl Thioglycolate → Methyl 3-amino-5-(pyridin-4-yl)thiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of sodium methoxide (2.12 g, 39.3 mmol) in methanol (59 mL) was added methyl thioglycolate (3.51 mL, 39.3 mmol). After 10 min, 3-chloro-3-(pyridin-4-yl)acrylonitrile (6.47 g, 39.3 mmol) was added, and the mixture was heated at 50° C. After 1 h, the mixture was concentrated to about a half volume at reduced pressure and poured into water (500 mL). Extraction with ethyl acetate/tetrahydrofuran (4:1, 500 mL), washing with brine, drying over magnesium sulfate, filtration and concentration at reduced pressure gave the title compound (8.81 g, 96%) as a yellow solid:

Provenance & Evidence