Diisopropylethylamine → HCID 64992279, compound

Participants

Reaction Steps

5-Bromo-1-methyl-1H-pyrazole-4-carboxylic acid (29.6 mmol), decahydro-quinoline (Aldrich Chemical Company, Inc., Milwaukee, Wis.; 4.9 g, 35.5 mmol), diisopropylethylamine (11 mL, 59.2 mmol), and PyBrop (bromo-tris-pyrrolidino-phophonium hexafluorophosphate) (Chem-Impex International, Inc., Wood Dale, Ill.; 16.6 g, 35.5 mmol) were mixed together in dry dichloromethane (70 mL) and dry dimethylformamide (20 mL). The mixture was stirred overnight at room temperature. At this time, the mixture was diluted with dichloromethane and extracted three times with water. The combined dichloromethane extracts were evaporated, and the residue was purified by flash chromatography, eluting with 0-10% ethyl acetate/hexanes to give 5-bromo-1-methyl-1H-pyrazol-4-yl)-(octahydro-quinolin-1-yl)-methanone (7.9 g, 82% yield).

Provenance & Evidence