1,2-Dichloroethane → 2-(Tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid methyl ester

Participants

Reaction Steps

A solution of benzo[b]thiophene-2,5-dicarboxylic acid 5-methyl ester (191.3 mg, 0.81 mmol), O -(Tetrahydro-pyran-2-yl)-hydroxylamine (93 mg, 0.79 mmol), EDC (231 mg, 1.20 mmol), HOBt (107 mg, 0.79 mmol) and DIEA (0.30 mL, 2.2 mmol) in anhydrous THF (8 mL) was allowed to stir at rt for three days and then concentrated. To the residue was added MeOH (1 mL) and water (10 mL) and Et2O (5 mL). After stirring for 2 h, the solid formed was washed with water (2×3 mL) and Et2O (5 mL), and dried to give 2-(tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid methyl ester as a pale solid). MS (EI): cal'd 252.0 (M−THP+H+), exp 252.1 (M−THP+H+).

Provenance & Evidence