Sodium Carbonate → HCID 178453659, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl {trans-3-[(2-chloro-5-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4yl)oxy]cyclobutyl}methylcarbamate (450 mg, 0.7 mmol), pyridin-3-ylboronic acid (95 mg, 0.8 mmol), 1,4-dioxane (10 mL), water (3 mL), sodium carbonate (94 mg, 0.9 mmol), PdCl2(dppf) (54 mg, 0.07 mmol) was stirred and heated at 70° C. for 1 hr. The reaction was diluted with ethyl acetate (60 mL) and water (15 mL). The organic layer was separated, washed with brine (20 mL), dried over Na2SO4 and evaporated to give a residue, which was purified via flash chromatography (eluting with a gradient of 0%-100% EtOAc in heptanes) to give the title compound (304 mg, 73% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.90 (d, J=1.83 Hz, 1H) 8.53 (dd, J=4.71, 1.41 Hz, 1H) 8.12 (dt, J=8.01, 1.86 Hz, 1H) 7.98 (s, 1H) 7.48 (dd, J=7.82, 4.89 Hz, 1H) 5.58 (s, 2H) 5.40 (t, J=6.60 Hz, 1H) 4.67 (br. s., 1H) 3.52-3.65 (m, 2H) 2.78 (s, 3H) 2.59-2.71 (m, 2H) 2.21-2.37 (m, 2H) 1.38 (s, 9H) 0.82-0.93 (m, 2H) −0.06 (s, 9H). m/z (APCI+) for C27H38ClN5O4Si 560.2 (M+H)+.

Provenance & Evidence