Sodium Carbonate → HCID 10163050, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 82 (0.046 g, 0.1 mmol) in EtOH/DME/toluene (1 mL, 2:1:1) was added to phenylvinylboronic acid (0.015 g, 0.1 mmol). A solution of Pd(PPh3)4 (0.006 g, 0.005 mmol) in DME (0.5 mL) and aqueous Na2CO3 (20 mg in 0.3 mL H2O, 0.2 mmol) were added. The reaction mixture was heated to 90° C. on a shaker for 15 min then concentrated, diluted with DMSO/MeOH (1:1, 1 mL) and purified by HPLC with 0.1% TFA, water, and CH3CN to provide the titled compound (8 mg, 17%). 1H NMR (500 MHz, CDCL3) δ 8.46 (d, J=8.4 Hz, 1H), 7.50 (m, 4H), 7.36 (dd, J=15.3, 7.8 Hz, 3H), 7.26 (m, 3H), 7.17 (t, J=8.1 Hz, 1H), 7.09 (s, 2H), 6.72 (d, J=9.0 Hz, 1H), 6.65 (m, 2H), 6.24 (s, 1H), 6.01 (s, 1 H), 3.95 (s, 3H), 2.97 (s, 3H); MS (CI, +Q1MS) m/e 483.

Provenance & Evidence