Sodium Carbonate → HCID 57801560, compound

Participants

Reaction Steps

To a solution of the intermediate from example 79 step F (50 mg, 0.079 mmol) in toluene (1 mL) was added phenyl boronic acid (10 mg, 0.079 mmol), Na2CO3 solution (2.0M, 79 uL) and tetrakis triphenyl phosphine palladium (0) (5 mg, 0.003 mmol). The resulting mixture was placed in the CEM microwave instrument for 10 min at a temperature of 100° C. and power 150 W. The reaction mixture was diluted with ethyl acetate and washed with saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 3:10 ethyl acetate-hexanes to give the desired product, a colorless oil. To a solution of this material in DCM (2 mL) was added trifluoroacetic acid (2 mL). The reaction was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and lyophilized from acetonitrile-water to give the title compound. 1H NMR (DMSO, 500 MHz): δ 8.5 (t, J=5.5 Hz, 1H), 7.91 (d, J=1.9 Hz, 2H), 7.81 (d, J=8.2 Hz, 2H), 7.78 (d, J=8.5 Hz, 2H), 7.74 (d, J=7.3 Hz, 2H), 7.58 (m, 3H), 7.51 (t, J=7.6 Hz, 2H), 7.42 (t, J=7.6 Hz, 1H), 7.25 (s, 1H), 7.15 (d, J=8.2 Hz, 2H), 5.56 (s, 2H), 3.45 (q, J=7.1 Hz, 2H), 2.47 (t, J=7.1 Hz, 2H). LC-MS: 2.73 min; (M+H)=570.1.

Provenance & Evidence