Sodium Carbonate → 1-Methylethyl 4-({[4'-(4-morpholinylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate

Participants

Reaction Steps

The title compound (10 mg, 8%) was prepared as a white solid from [4-(4-morpholinylsulfonyl)phenyl]boronic acid (54 mg, 0.2 mmol), 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 9, Step 2, 71 mg, 0.2 mmol), Pd(PPh3)2Cl2 (50 mg, 0.07 mmol), 2M Na2CO3 (1 mL) and DME (1 mL) in a manner similar to Example 21, Step 3, and worked up in a manner similar to Example 9, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.78 (m, 2H), 7.70 (m, 2H), 7.54 (d, 2H, J=8.8 Hz), 6.99 (d, 2H, J=8.8 Hz), 4.97-4.86 (m, 1H), 4.22 (bs, 2H), 3.86 (d, 2H, J=6.4 Hz), 3.78-3.73 (m, 4H), 3.07-3.01 (m, 4H), 2.84-2.74 (m, 2H), 2.05-1.95 (m, 1H), 1.91-1.81 (m, 2H), 1.37-1.27 (m, 2H), 1.25 (d, 6H, J=6.4 Hz); LRMS (ESI), m/z 503 (M+H).

Provenance & Evidence