5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one → 1-(1,3-Dimethyl-1H-pyrazol-4-yl)-3-methyl-8-(2-oxo-2,3-dihydro-1H-indol-5-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Participants

Reaction Steps

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A, 40 mg, 0.106 mmol) and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one (Combi-Blocks, San Diego, USA, 35 mg, 0.128 mmol) to give the title compound as an off-white solid. (HPLC: tR 2.40 min (Method A); M+H=425 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 10.52 (s, 1H), 8.92 (s, 1H), 8.17 (s, 1H), 8.05-8.03 (m, 1H), 7.86-7.83 (m, 1H), 7.46 (s, 1H), 7.33-7.29 (m, 2H), 6.90-6.88 (m, 1H), 3.94 (s, 3H), 3.57 (s, 3H), 3.54 (s, 2H), 1.93 (s, 3H))

Provenance & Evidence