Potassium Carbonate → [2-(4-Bromopyrazol-1-yl)ethyl]dimethylamine

To a solution of 4-bromo-1H-pyrazole (5 g, 34 mmol) in DMF were added K2CO3 (11.75 g, 85.03 mmol, 2.5 eq.) and 2-chloro-N,N-dimethylethanamine HCl (7.35 g, 51 mmol, 1.5 eq) and the mixture was stirred at RT for 12 h. The mixture was quenched with water and extracted with DCM (3×150 ml). The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 1% methanol in DCM) to give the product in 86% yield (6.4 g). 1H NMR (300 MHz, DMSO-d6): δ 7.95 (s, 1H), 7.25 (s, 1H), 4.18 (t, 2H), 2.61 (t, 2H), 2.15 (s, 6H); LC-MS (ESI): Calculated mass: 218.09; Observed mass: 219.8[M+H]+ (RT: 0.439 min).

1. customThe mixture was quenched with water
2. extractionextracted with DCM (3×150 ml)
3. washThe combined organic layer was washed with water, brine
4. dry with materialdried over sodium sulphate
5. distillationThe solvent was distilled off

ORD-Eintrag

ord-1a0d515778a9411c8eef06070d89d8c2

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09447091B2