Sodium Carbonate → HCID 50906138, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-fluorophenyl)-3-methyl-N-(2-morpholino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinolin-4-amine (44.0 mg, 0.082 mmol), 4-bromopyridin-2-amine (14.1 mg, 0.082 mmol), dichlorobis(triphenylphosphine)palladium(II) (5.73 mg, 8.16 μmol) and sodium carbonate (14.68 mg, 0.245 mmol) in 1,4-dioxane (2.00 mL) and water (0.500 mL) in a microwave vessel was purged with nitrogen then heated in a microwave at 120° C. for 60 min, after which time LC-MS indicated no starting material remained and desired product was present. The reaction was partitioned between 30 mL EtOAc and 20 mL water. The organic separation was stirred over anhydrous magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a yellow film. The product was isolated by preparative scale reversed-phase HPLC, affording a colorless solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.11 (1H, d, J=8.2 Hz), 7.92 (1H, d, J=5.5 Hz), 7.84 (1H, d, J=8.6 Hz), 7.60-7.69 (1H, m), 7.56 (1H, td, J=7.4, 2.0 Hz), 7.34-7.51 (2H, m), 7.26 (1H, t, J=7.4 Hz), 6.99-7.21 (5H, m), 6.63 (2H, dd, J=7.4, 2.3 Hz), 6.43 (1H, br. s.), 4.44 (2H, d, J=1.2 Hz), 3.88 (4H, t, J=4.7 Hz), 2.94-3.23 (4H, m), 2.15 (3H, d, J=2.3 Hz). Mass Spectrum (ESI) m/e=506.2 (M+1).

Provenance & Evidence