Sodium Carbonate → HCID 58958602, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (4-bromo-3-tert-butyl-1-methyl-1H-pyrazol-5-yl)carbamate (Intermediate I, 1.7 g, 5.12 mmol), pyridine-3-boronic acid (1.26 g, 10.23 mmol), and Pd(PPh3)4 (295 mg, 0.26 mmol) were dissolved in ethanol (25 mL), and Na2CO3 (2 M aqueous solution, 25 mL) was added. The mixture was degassed for 10 min. The reaction mixture was then heated to 80° C. for 16 h. The mixture was diluted with ethyl acetate, the solid was filtered off, and the filtrate was treated with TFA (5 mL). The mixture was stirred for 30 min before being concentrated under reduced pressure. The crude was dissolved in methanol and filtered though a C8-silica plug. HPLC purification with gradient elution from 5 to 60% acetonitrile in water afforded 300 mg (25%) of the title compound. 1H NMR (300 MHz, CD3OD) δ 8.73 (d, 1H), 8.64 (s, 1H), 8.14 (d, 1H), 7.81 (dd, 1H), 3.73 (s, 3H), 1.20 (s, 9H). ES-MS m/z 231.2 (MH+); HPLC RT (min) 0.23.

Provenance & Evidence