Cesium carbonate → HCID 131733599, compound

Participants

Reaction Steps

A 20 mL vial equipped with a septum cap and stir bar was charged with cesium carbonate (977 mg, 3.00 mmol), 3-bromo-5-methoxypyridine (188 mg, 1.00 mmol), potassium[2-(tert-butoxycarbonylamino)ethyl]trifluoroborate (301 mg, 1.20 mmol), di-(1-adamantyl)-n-butylphosphine (35.8 mg, 0.100 mmol) and palladium (II) acetate (11.2 mg, 0.050 mmol). Toluene (3 mL) and water (2 mL) were added, and the vial was purged with nitrogen gas and sealed. The mixture was stirred vigorously at 80° C. for 24 h, cooled to room temperature and the aqueous layer was removed. The organic layer was dried with sodium sulfate and the crude product solution was purified by silica gel chromatography (0-10% MeOH in DCM) to provide tert-butyl (2-(5-methoxypyridin-3-yl)ethyl)carbamate as a colorless syrup (153 mg, 0.606 mmol, 61%). 1H NMR (CDCl3, 500 MHz): δ (ppm) 8.21 (d, J=6.14 Hz, 1H), 8.09 (d, J=1.58 Hz, 1H), 6.98-7.16 (m, 1H), 4.53-4.90 (m, 1H), 3.87 (s, 3H), 3.33-3.47 (m, 2H), 2.82 (t, J=6.78 Hz, 2H), 1.46 ppm (s, 9H).

Provenance & Evidence