Sodium Carbonate → HCID 46896832, compound

Participants

Reaction Conditions

Reaction Steps

To a flask charged with Na2CO3 (2.0 M in water, 132 μL, 0.263 mmol), Pd(PPh3)4 (10.1 mg, 8.77 μmol) and (4-methylphenyl)boronic acid (36.5 mg, 0.175 mmol) was added a solution of the product from Step A (50 mg, 0.088 mmol) in DMF, then the mixture was stirred at 60° C. overnight. After cooling to RT, the mixture was purified by preparative reverse phase HPLC eluting with 50-100% acetonitrile/water+0.1% TFA to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 7.81 (d, J=8.5 Hz, 2H); 7.43 (d, J=7.5 Hz, 4H); 7.36 (t, J=8.5 Hz, 4H); 7.35 (d, J=8.5 Hz, 1H); 7.28 (d, J=3.0 Hz, 1H); 7.26 (d, J=8.0 Hz, 2H); 7.19 (dd, J=8.5, 2.5 Hz, 1H); 5.77 (d, J=7.0 Hz, 1H); 3.65-3.61 (m, 2H); 3.31 (m, 1H), 3.25 (s, 3H); 2.65 (t, J=6.5 Hz, 2H); 1.88-1.86 (m, 1H); 1.63-1.61 (m, 1H); 1.16-1.11 (m, 2H); 0.79 (t, J=7.0 Hz, 3H); LC1 1.27 min. (M+H)+ 581.

Provenance & Evidence