Cesium carbonate → HCID 67517143, compound

Participants

Reaction Steps

To a solution of methyl 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1 g, 2.7 mmol, 1.0 eq) and tert-butyl 3-aminopiperidine-1-carboxylate (659 mg, 3.3 mmol, 1.2 eq) in PhCH3 (20 mL) was added Pd(OAc)2 (65 mg, 0.27 mmol, 0.1 eq), xantphos (250 mg, 0.41 mmol, 0.15 eq) and. Cs2CO3 (2.64 g, 8.1 mmol, 3.0 eq) and the mixture was heated at 100° C. for 16 h. After cooling to rt, the mixture was filtered and the filtrate was concentrated in vacuo to afford an oil which was purified by silica gel column chromatography (PE/EA=8:1) to give the title compound as white solid (667 mg, yield: 46%). 1H NMR (400 MHz, CDCl3) δ: 8.91 (d, 1H), 8.72 (s, 1H), 7.96 (d, 2H), 7.45 (d, 1H), 7.18 (d, 2H), 3.77 (s, 3H), 3.67-3.57 (m, 1H), 3.13-2.97 (m, 2H), 2.29 (s, 3H), 1.98-1.96 (m, 2H), 1.83-1.67 (m, 2H), 1.64-1.46 (m, 3H), 1.40-1.25 (m, 9H). ESI-MS (M+H)+: 529.20.

Provenance & Evidence