Sodium Carbonate → HCID 66673255, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [4-(methylthio)phenyl]boronic acid (66 mg, 0.39 mmol), 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 81, Step 1, 140 mg, 0.39 mmol), PdCl2(PPh3)2 (50 mg), 2M Na2CO3 (1 mL) and DME (2 mL) was stirred and heated in a microwave at 120° C. for 10 min, cooled to ambient temperature, and the organics were separated. The aqueous phase was washed with EtOAc. The organics were combined, dried over MgSO4, filtered, and the filtrate was concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 50% EtOAc/hexanes to give 140 mg (90%) of 1-methylethyl 4-[({6-[4-(methylthio)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.32 (d, 1H, J=2.8 Hz), 7.84 (d, 2H, J=8.5 Hz), 7.60 (d, 1H, J=8.8 Hz), 7.30 (d, 2H, J=8.5 Hz), 7.22 (bs, 1H), 4.90 (septet, 1H, J=6.3 Hz), 4.20 (bs, 2H), 3.87 (d, 2H, J=6.3 Hz), 2.85-2.70 (m, 2H), 2.50 (s, 3H), 2.04-1.94 (m, 1H), 1.90-1.75 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 401 (M+H).

Provenance & Evidence