Toluene → HCID 11215412, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave tube charged with (±)-N-(1-(6-bromopyridin-2-yl)-2-(7-methyl-1H-indazol-5-yl)ethyl)-4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxamide (24.6 mg, 0.0418 mmol, 1.0 equiv) was added phenyl boronic acid (7.1 mg, 0.0585 mmol, 1.4 equiv), Pd(PPh3)4 (4.8 mg, 0.1 equiv), toluene (1 mL), ethanol (0.2 mL), and potassium carbonate solution (2M, 0.085 mL). The vial was sealed and heated by microwave at 140° C. for 30 min. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. Flash column chromatography (10% methanol/methylene chloride) afforded the desired product (20 mg, 81.6%) as an off-white solid: MS (ESI) [M+H]+=586. 1H-NMR (400 MHz, CDCl3) δ 8.00-7.86 (m, 3H), 7.65-6.82 (m, 12H), 6.74 (d, J=7.2 Hz, 1H), 6.66 (d, J=8.0 Hz, 1H), 6.32 (br., 1H), 5.35-5.20 (m, 1H), 4.62-4.48 (m, 1H), 4.30-4.08 (m, 4H), 3.40 (dd, J=13.2 and 4.2 Hz, 1H), 3.13 (dd, J=13.2 and 8.4 Hz, 1H), 3.02-2.83 (m, 2H), 2.42 (s, 3H), 1.80-1.55 (m, 4H). HPLC tR=1.51 min.

Provenance & Evidence