Sodium hydride → HCID 67388455, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (0.498 g, 60% in mineral oil) was added to a stirred solution of 4-bromo-N,N-dimethyl-1H-pyrazol-3-amine (1.97 g) dissolved in DMF (20 ml) under argon. The resulting mixture was stirred at 23° C. for 30 minutes. A solution of Tert-butyl 4-methylsulfonyloxypiperidine-1-carboxylate (3.19 g) in DMF (10 ml) was added and the reaction mixture was stirred at 95° C. for 5 hours and left at 23° C. overnight. DMF was evaporated and the residue was taken up in dichloromethane, washed with H2O and sat NaCl. The organic was dried (magnesium sulphate), filtered and concentrated. The residue was purified by flash chromatography on silica gel eluting with 0 to 30% ethyl acetate in petroleum ether. The solvent was evaporated to afford tert-butyl 4-(4-bromo-3-dimethylamino-pyrazol-1-yl)piperidine-1-carboxylate (1.700 g) as a clear colorless oil which crystallised on standing. NMR Spectrum: (DMSOd6) 1.40 (s, 9H), 1.65 (d, 1H), 1.71 (d, 1H), 1.89-1.87 (m, 2H), 2.74 (s, 6H), 2.85 (bs, 2H), 3.93-4.06 (m, 2H), 4.09-4.17 (m, 1H), 7.82 (s, 1H); Mass spectrum: M+H+ 373-375

Provenance & Evidence