Diisopropylethylamine → 2-(2,5-Dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid amide

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Reaction Conditions

Reaction Steps

Diisopropylethylamine (0.574 mL) is added to a stirred suspension of 2-(2,5-dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid (1.02 g, 3.14 mmol) in anhydrous dichloromethane (20 mL) at 0° C. under nitrogen to form a clear solution. The solution is treated dropwise with 7M NH3/MeOH (0.493 mL, 3.45 mmol) to form a suspension. Powdered 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.46 g, 3.30 mmol) is added to the mixture and the resultant mixture is allowed to stir at 0° C. for 2 hours and at room temperature for 5 hours. Diethyl ether (15 mL) is added in small portions to the mixture. The mixture is stirred for another 20 minutes before filtration. After drying, the title compound is obtained as a tan solid and is used without further purification (0.994 g).

Provenance & Evidence