Sodium Carbonate → HCID 66673224, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,1-dimethylethyl 4-{[(6-bromo-3-pyridinyl)amino]carbonyl}-1-piperidinecarboxylate (1.75 g, 4.55 mmol), [4-(methylsulfonyl)phenyl]boronic acid (911 mg, 4.55 mmol), 2M Na2CO3 (5 mL) and Pd(PPh3)2Cl2 (400 mg, 0.57 mmol) in DME (10 mL) was stirred at 80° C. overnight. The mixture was cooled to ambient temperature, and the organic phase was separated and concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 5% MeOH/CH2Cl2 to give 1.41 g (68%) of 1,1-dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}amino)carbonyl]-1-piperidinecarboxylate as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.74 (bs, 1H), 8.57-8.46 (m, 1H), 8.16 (d, 2H, J=8.5 Hz), 8.03 (d, 2H, J=8.4 Hz), 7.81 (d, 1H, J=8.7 Hz), 4.28-4.11 (m, 2H), 3.07 (s, 3H), 2.85-2.74 (m, 2H), 2.55-2.44 (m, 1H), 2.00-1.80 (m, 2H), 1.82-1.69 (m, 2H), 1.45 (s, 9H); LRMS (ESI), m/z 460 (M+H).

Provenance & Evidence