N-Methylbenzylamine → 2-(4-bromo-1H-pyrazol-1-yl)-N-methyl-N-(phenylmethyl)ethanamine

Participants

Reaction Conditions

Reaction Steps

4-bromo-1-(2-chloroethyl)-1H-pyrazole (317 mg, 1.513 mmol, for a preparation see Intermediate 54) was dissolved in N,N-dimethylformamide (DMF) (5 mL) and cesium carbonate (740 mg, 2.270 mmol) added with N-methyl-1-phenylmethanamine (0.973 mL, 7.57 mmol, available from Aldrich). The mixture was heated to 80° C. for 3 hours then allowed to stir at 80° C. overnight. The mixture was cooled to room temperature and loaded on to a 20 g SCX cartridge. The SCX was eluted with MeOH (100 ml) and 2M methanolic ammonia (100 ml). The basic fraction was evaporated to a colourless oil, loaded on to a 25+M Biotage silica column and eluted with a gradient of 0 to 2.5% 2M methanolic ammonia in DCM. The product containing fractions were evaporated to a pale yellow oil (155 mg). LCMS (Method C): Rt=0.67, MH+=294

Provenance & Evidence