Sodium Carbonate → HCID 86679634, compound

Participants

Reaction Steps

To a vial was added 2-chloro-5-iodo-4-(3-nitrophenoxy)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (333.7 mg, 0.61 mmol), pyridin-3-ylboronic acid (79 mg, 0.64 mmol, 1.05 mol eq), 1,4-dioxane (4 mL), water (1 mL), Na2CO3 (78 mg, 0.73 mmol, 1.2 mol eq) and Pd(PPh3)2Cl2 (21 mg, 0.05 mol eq). The reaction vial was capped, stirred at rt for 1 hr and was then heated to 60° C. (block temperature) for 2 days (note: the reaction progress was monitored by LCMS after couple hours and more pyridin-3-ylboronic acid was added as needed). The reaction was diluted with ethyl acetate (100 mL) and water (20 mL) and the organic layer was separated, washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and evaporated to give crude product (TLC: Rf 0.3 in 50% ethyl acetate-50% heptane). The crude product was purified on silica gel to give the title compound as a light yellow solid (266 mg, 88% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.01 (d, J=2.01 Hz, 1H) 8.54 (dd, J=4.78, 1.51 Hz, 1H) 8.38 (t, J=2.14 Hz, 1H) 8.23 (dd, J=8.06, 2.01 Hz, 2H) 8.15 (s, 1H) 7.86-7.93 (m, 1H) 7.77-7.85 (m, 1H) 7.50 (dd, J=7.93, 4.66 Hz, 1H) 5.68 (s, 2H) 3.58-3.74 (m, 2H) 0.83-1.02 (m, 2H) 0.00 (s, 9H). m/z (APCI+) for C23H24ClN5O4Si 498.0 (M+H)+.

Provenance & Evidence