Cesium carbonate → HCID 86731678, compound

Participants

Reaction Conditions

Reaction Steps

To a flask containing 1-[(6-bromopyridin-2-yl)methoxy]-2-methylpropan-2-ol (500 mg, 1.92 mmol), benzyl carbamate (349 mg, 2.31 mmol), Pd2(dba)3 (88 mg, 0.096 mmol), Xantphos (111 mg, 0.192 mmol) and cesium carbonate (939 mg, 2.88 mmol) was added degassed dioxane (15 mL). The flask was evacuated/purged with argon 5 times. The reaction mixture was heated to 80° C. for 18 hours. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-50% ethyl acetate/hexanes, linear gradient) to afford benzyl {6-[(2-hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}carbamate. MS ESI calc'd. for C18H23N2O4 [M+H]+ 331. found 331. 1H NMR (500 MHz, CDCl3) δ 7.88 (d, J=8.4 Hz, 1H), 7.69 (t, J=7.9 Hz, 1H), 7.46-7.30 (m, 5H), 7.07 (d, J=7.5 Hz, 1H), 5.22 (s, 2H), 4.57 (s, 2H), 3.39 (s, 2H), 1.24 (s, 6H).

Provenance & Evidence