Potassium Carbonate → HCID 86727566, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.230 g, 0.465 mmol), K2CO3 (0.129 g, 0.930 mmol), (2-fluorophenyl)boronic acid (0.098 g, 0.698 mmol) and PdCl2(dppf)-CH2Cl2 adduct (0.038 g, 0.047 mmol) in dioxane (4 mL) and water (0.66 mL) was heated at 90° C. for 14 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by prep-TLC (eluting with 10% EtOAc in petroleum ether) to give 3-[7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.220 g, 93%) as a pale solid. 1H-NMR (400 MHz, CDCl3) δ 8.09-8.00 (brs, 1H), 7.41-7.31 (m, 1H), 7.24-7.19 (m, 2H), 7.19-7.08 (m, 1H), 6.73 (s, 1H), 6.46 (s, 1H), 4.79-4.66 (m, 1H), 4.64-4.47 (m, 1H), 3.55-3.08 (m, 4H), 2.16-1.93 (m, 2H), 1.58-1.55 (m, 3H), 1.50-1.37 (m, 12H). LC/MS (Table 1, Method 25) Rt=0.895 min; MS m/z: 510 [M+1]+.

Provenance & Evidence