Benzyl Alcohol → HCID 68008361, compound

Participants

Reaction Conditions

Reaction Steps

3-Bromo-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one (1.2 g, 3.5 mmol), benzyl alcohol (3.62 mL, 35.0 mmol), CuI (67.0 mg, 0.35 mmol), 1,10-phenanthroline (127.0 mg, 0.7 mmol) were mixed with Cs2CO3 (1.69 g, 5.2 mmol) in toluene (15.0 mL). The reaction was degassed, sealed in a microwave tube, heated to 110° C. for 1.5 day. The reaction mixture was passed through a Celite pad, diluted with H2O (50.0 mL), extracted with EtOAc (40.0×3 mL). The organic layers were combined, dried over MgSO4, concentrated in vacuo and purified by automated silica gel column chromatography (EtOAc/hexanes 0-60%). The compound was obtained as a sticky oil (1.08 g, 83%). 1HNMR (400 MHz, CDCl3) δ 8.39 (br s, 1H), 8.01 (d, J=3.2 Hz, 1H), 7.48-7.37 (overlapped, 5H), 7.30-7.27 (overlapped, 2H), 6.90 (d, J=8.8 Hz, 2H), 5.17 (s, 2H), 4.74 (s, 2H), 3.82 (s, 3H), 3.55 (t, J=6.8 Hz, 2H), 3.08 (t, J=6.8 Hz, 2H); LC-MS (M+H)=375.1.

Provenance & Evidence