Cesium carbonate → HCID 59596249, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-Bromophenyl)-1-[6-(trifluoromethyl)pyridin-3-yl]-1H-isoindol-3-amine acetate (Example 52, 0.046 g, 0.09 mmol), pyrimidine-5-boronic acid (0.023 g, 0.186 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (0.004 g, 0.0046 mmol) and cesium carbonate (0.092 g, 0.284 mmol) were dissolved in 1,2-dimethoxy ethane:ethanol:water (6:3:1, 2 mL) and heated to 130° C. for 20 minutes in a microwave oven. Additional [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (0.004 g, 0.0046 mmol) was added and the resulting mixture was heated to 130° C. for additional 20 minutes. After cooled to ambient temperature the mixture was filtered and purified by preparative HPLC to give 0.011 g (26% yield) of the title compound. 1H NMR (MeOD) δ 9.12 (s, 1 H), 9.02-8.95 (m, 2 H), 8.64 (d, J=2.02 Hz, 1 H), 8.06-7.92 (m, 2 H), 7.80 (dd, J=7.96, 2.40 Hz, 2 H), 7.76-7.69 (m, 2 H), 7.68-7.61 (m, 2 H), 7.57 (t, J=7.83 Hz, 1 H), 7.49-7.41 (m, 1 H), 1.94 (s, 2 H); MS (ES) m/z 430 [M−H]−, m/z 432 [M+H]+.

Provenance & Evidence