tert-butyl (3R)-3-aminopiperidine-1-carboxylate → (R)-tert-butyl 3-((1-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)amino)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of Pd2(dba)3 (1.53 g, 1.68 mmol), BrettPhos (1.86 g, 3.36 mmol) in toluene (40 mL) under N2 atmosphere was stirred for 20 min. NaOtBu (3.23 g, 33.6 mmol), the compound from Step 1 7-chloro-1-methyl-1H-pyrrolo[2,3-c]pyridine (2.80 g, 16.8 mmmol) and tert-butyl (3R)-3-aminopiperidine-1-carboxylate (4.04 g, 20.2 mmol) were added. The reaction was stirred at 105° C. for 3 h. The reaction mixture was poured into water (20 mL) and extracted with EtOAc (3×20 mL). The organic layers were dried over Na2SO4, filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with a gradient of 17-50% EtOAc/petroleum ether to give the title compound as a brown solid (5.2 g, 94%).

Provenance & Evidence