Sodium Carbonate → HCID 72201877, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 44.2, 60 mg, 0.152 mmol) and NaOMe (24.58 mg, 0.455 mmol) in anhydrous MeOH (250 μL) was stirred for 2 h at 80° C. in a sealed MW vial. Pyrimidin-5-ylboronic acid (56.4 mg, 0.455 mmol), Pd(PPh3)2Cl2 (10.65 mg, 0.015 mmol), Na2CO3 (80 mg, 0.758 mmol), water (160 μL) and EtOH (80 μL) and DME (600 μL) were added, and the vial was resealed and the RM stirred at 80° C. for 16 h. The RM was diluted with 3 mL of THF and stirred with Si-Thiol (59.7 mg, 0.076 mmol) for a 2 h and the combined filtrates were evaporated to dryness under reduced pressure. The residue was purified by flash chromatography (RediSep® Silica gel column, 4 g, DCM/MeOH+1% NH4OH from 1% to 10% MeOH+1% NH4OH) and preparative HPLC (Condition 8, 30% for 0.2 min then 30% to 60% in 12 min) to afford the title compound as a white solid. UPLC-MS (Condition 1) tR=2.47 min, m/z=391.0 [M+H]+, m/z=389.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 4.02 (s, 3H) 7.40 (d, J=8.3 Hz, 2H) 7.88 (d, J=9.3 Hz, 2H) 8.48 (d, J=2.4 Hz, 1H) 8.86 (d, J=2.4 Hz, 1H) 9.13 (s, 2H) 9.23 (s, 1H) 10.47 (s, 1H).

Provenance & Evidence