Sodium Carbonate → HCID 59375027, compound

Participants

Reaction Conditions

Reaction Steps

Step 2 A suspension of impure 7-(isopropylamino)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1-carboxamide (60 mg, 0.053 mmol), 7-(3-bromo-2-methylphenyl)imidazo[1,2-a]pyrazin-8(7H)-one TFA salt (Intermediate 11-1, 22.3 mg, 0.053 mmol), tetrakis(triphenylphosphine)palladium (3.1 mg, 0.003 mmol) and 2 M aqueous sodium carbonate (0.080 mL, 0.160 mmol) in toluene-ethanol (4:1, 1.3 mL) was heated under nitrogen at 90° C. overnight. The mixture was concentrated and the residue was purified by preparative HPLC. The appropriate effluent fractions were concentrated and the residue was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was dried and concentrated to provide 7-(isopropylamino)-4-(2-methyl-3-(8-oxoimidazo[1,2-a]pyrazin-7(8H)-yl)phenyl)-9H-carbazole-1-carboxamide as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 10.83-10.99 (1H, m), 8.01 (1H, br. s.), 7.83 (1H, dd, J=4.5, 1.0 Hz), 7.68-7.77 (1H, m), 7.59-7.67 (1H, m), 7.38-7.50 (3H, m), 7.24-7.38 (2H, m), 7.08 (1H, dd, J=8.4, 5.9 Hz), 6.76-6.87 (1.55H, m), 6.73 (1H, dd, J=7.4, 1.9 Hz), 6.48 (0.45H, d, J=8.8 Hz), 6.13-6.29 (1H, m), 5.44 (1H, t, J=8.3 Hz), 3.40-3.55 (1H, m), 1.70 (3H, d, J=11.4 Hz), 1.09 (6H, td, J=5.8, 3.4 Hz). Mass spectrum m/z 491.3 (M+H)+.

Provenance & Evidence