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

Temperature

105 °C

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%).

1. extractionextracted with EtOAc (3×20 mL)
2. dry with materialThe organic layers were dried over Na2SO4
3. filtrationfiltered
4. concentrationthe filtrate was concentrated in vacuo
5. customThe residue was purified by silica gel column chromatography
6. washeluting with a gradient of 17-50% EtOAc/petroleum ether

ORD record

ord-c656875441234c8a95f0cc918694e41d

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227956B2