Sodium Carbonate → HCID 86710768, compound

Participants

Reaction Steps

A solution of ((2S)-methyl 2-(7-(4-allylchroman-6-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.430 g, 0.711 mmol), (2-hydroxyphenyl)boronic acid (0.196 g, 1.423 mmol) and 2.0 M aq. Na2CO3 (1.1 ml, 2.1 mmol) in DMF (7 ml) was sparged with nitrogen for 10 min, treated with Pd(Ph3P)4 (0.058 g, 0.050 mmol), then sparged for 5 min. The reaction was stirred for 90 min, then cooled, diluted with water (20 mL) and extracted into Et2O (2×50 mL). The combined extracts were dried (MgSO4), filtered, and concentrated and the residue was purified by biotage (24 g SiO2, 0% (3 CV), 0-60% (15 CV), 60% (2 CV), EtOAc in hexanes) to afford the desired product (0.360 g, 0.572 mmol, 80% yield) as a pale yellow glassy solid. 1H NMR (500 MHz, CDCl3) δ: 8.07-7.89 (m, 2H), 7.70 (s, 1H), 7.60-7.49 (m, 2H), 7.49-7.36 (m, 2H), 7.34-7.29 (m, 2H), 7.07-6.97 (m, 3H), 6.95-6.90 (m, 1H), 5.96-5.71 (m, 1H), 5.37-5.19 (m, 2H), 5.16-4.97 (m, 2H), 4.39-4.25 (m, 2H), 3.88-3.79 (m, 3H), 3.12-2.88 (m, 1H), 2.72-2.63 (m, 3H), 2.61-2.32 (m, 1H), 2.22-2.08 (m, 1H), 2.02-1.88 (m, 1H), 1.06-0.92 (m, 9H). LCMS (M+H)=618.5.

Provenance & Evidence