Sodium Bicarbonate → HCID 72203421, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-6-(3,6-dihydro-2h-pyran-4-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 44.1, 160 mg, 0.361 mmol), pyrimidin-5-ylboronic acid (89 mg, 0.722 mmol), Pd(PPh3)2Cl2 (25 mg, 0.036 mmol), aq. 2 M NaHCO3 (0.541 mL, 1 mmol) and DME (1.5 mL) were added to a vial, which was sealed, evacuated/purged with argon and the RM was stirred at 90° C. for 1.5 h. The RM was diluted with EtOAc, washed with brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (RediSep® Silica gel column, DCM/MeOH from 2 to 5% MeOH) and treated with Si-Thiol (90 mg) in MeOH to afford the title product as a solid. HPLC (Condition 3) tR=4.99 min, UPLC-MS (Condition 2) m/z=443.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.39-2.60 (m, 2H) 3.74 (t, J=5.47 Hz, 2H) 3.90-4.00 (m, 2H) 5.58 (s, 1H) 7.39 (d, J=8.99 Hz, 2H) 7.77-7.92 (m, 2H) 8.40 (d, J=1.96 Hz, 1H) 8.94 (s, 2H) 9.12 (d, J=1.00 Hz, 1H) 9.21 (s, 1H) 10.60 (s, 1H).

Provenance & Evidence