Sodium Carbonate → HCID 66673331, compound

Participants

Reaction Steps

1-Methylethyl 4-{[(6-{4-[(2-amino-2-oxoethyl)thio]phenyl}-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (0.139 g, 75%) was prepared as a light yellow solid from {4-[(2-amino-2-oxoethyl)thio]phenyl}boronic acid (0.11 g, 0.50 mmol), 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (Example 81, Step 1, 0.15 g, 0.42 mmol), 2M Na2CO3 (2 mL), Pd(PPh3)2Cl2 (30 mg, 0.04 mmol) and DME (2 mL) in a manner similar to Example 21, Step 3. 1H NMR (400 MHz, CDCl3): δ 8.36 (d, 1H, J=2.5 Hz), 7.90 (d, 2H, J=8.2 Hz), 7.65 (d, 1H, J=8.8 Hz), 7.38 (d, 2H, J=8.2 Hz), 7.35-7.25 (m, 1H), 6.65 (bs, 1H), 5.41 (bs, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.23 (bs, 2H), 3.90 (d, 2H, J=6.3 Hz), 3.67 (s, 2H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 444 (M+H).

Provenance & Evidence