Potassium Phosphate, Tribasic → HCID 118195148, compound

Participants

Reaction Conditions

Reaction Steps

(R)-5-Bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1, 60 mg, 0.134 mmol), (6-methoxypyridin-3-yl)boronic acid (25.2 mg, 0.161 mmol), Pd2(dba)3 (2.463 mg, 2.69 μmol), 2-diclyclohexylphosphino-2′,4′,6′-triisoprophylbiphenyl (2.56 mg, 5.38 μmol) and K3PO4 (86 mg, 0.403 mmol) were added to a MW vial. The vial was sealed, evacuated/purged with argon, and BuOH (269 μL) was added. The RM was stirred at 100° C. for 16 h, diluted with THF (1 mL), treated with Si-Thiol (Silicycle, 1.27 mmol/g, 52.9 mg, 0.067 mmol), filtered and the filtrate was evaporated off under reduced pressure to give a residue which was purified by preparative HPLC (Condition 12, from 30% to 60% in 12 min.) to afford the title compound as a white solid. UPLC-MS (condition 1) tR=2.36 min, m/z=475.2 [M+H]+, m/z=473.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.68-1.78 (m, 1H) 1.77-1.90 (m, 1H) 2.93 (d, J=11.74 Hz, 1H) 3.18-3.26 (m, 2H) 3.35-3.46 (m, 1H) 3.91 (s, 3H) 4.20 (br. s, 1H) 4.83 (d, J=3.42 Hz, 1H) 6.91 (d, J=8.56 Hz, 1H) 7.34 (d, J=8.56 Hz, 2H) 7.72 (dd, J=8.56, 2.45 Hz, 1H) 7.86 (d, J=9.05 Hz, 2H) 7.97 (d, J=2.20 Hz, 1H) 8.21 (d, J=2.45 Hz, 1H) 8.74 (d, J=2.20 Hz, 1H) 10.14 (s, 1H).

Provenance & Evidence