Potassium Carbonate → HCID 86727601, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-7-bromo-6-((3R,4R)-1,3-dimethyl-piperidin-4-yl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.050 g, 0.123 mmol), (2-fluoro-3-methoxyphenyl)boronic acid (0.025 g, 0.147 mmol), K2CO3 (0.034 g, 0.246 mmol) and PdCl2(dppf)-CH2Cl2 adduct (0.020 g, 0.025 mmol) in dioxane (3 mL) and water (0.5 mL) was stirred at 90° C. overnight. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by preparative TLC (eluting with 17% MeOH in EtOAc) to give (R)-6-((3R,4R)-1,3-dimethyl-piperidin-4-yl)-7-(2-fluoro-3-methoxy-phenyl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.0248 g, 45%) as a solid. 1H NMR (400 MHz, CD3OD): δ 7.14 (m, 2H), 6.96-6.90 (m, 1H), 6.81-6.72 (m, 2H), 4.95-4.91 (m, 1H), 4.60 (d, J=13.2 Hz, 2H), 3.90 (s, 3H), 3.13 (m, 1H), 3.00-2.74 (m, 2H), 2.34 (m, 3H), 2.19 (m, 2H), 2.14 (m, 1H), 1.67 (m, 2H), 1.48 (m, 3H), 0.89-0.79 (m, 3H). LC/MS (Table 1, Method 4) Rt=2.075 min.; MS m/z: 453 [M+H]+. SFC (Table 2, Method 27), Rt=3.239 min.

Provenance & Evidence