Potassium Carbonate → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of the title compound from Example 19 Step I (20 mg, 0.026 mmol) Pd(PPh3)4 (10.7 mg, 0.009 mmol), K2CO3 (11 mg, 0.08 mmol), trimethyl boroxine (11.6 mg, 0.09 mmol), and dioxane (0.5 mL) was heated in a microwave reactor at 140° C. for 1 h, cooled, diluted with hexanes and passed through a pad of silica gel eluted by dichloromethane. The solvent was removed in vacuo. Treatment with a mixture of 1,4-dioxane (0.1 mL), MeOH (0.1 mL) and 3 N NaOH (0.1 mL) at 50° C. for 15 min, followed by reverse phase HPLC using a YMC C-18 column (45 to 95% acetonitrile in water, each with 0.1% v/v TFA) provided the title compound: LCMS m/z 618.8 [M+H]+; 1H NMR (400 MHz, acetone-d6), δ 8.17 (s, 1H), 8.08 (s, 1H), 7.75 (d, J=2.1 Hz, 1H), 7.48 (s, 1H), 7.41 (d, J=8.1 Hz, 2H), 7.27 (d, J=8.1 Hz, 2H), 7.20 (dd, J=8.4 Hz, 2.1 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H), 2.43 (s, 3H), 2.29 (s, 3H), 2.59 (m, 1H), 1.96 (m, 2H), 1.67-1.39 (m, 4H).

Provenance & Evidence