Benzyl Alcohol → HCID 89783920, compound

Participants

Reaction Conditions

Reaction Steps

NaH (60% in mineral oil; 0.071 g, 1.763 mmol) was suspended in 1 mL DMF. Phenylmethanol (0.183 ml, 1.763 mmol) was added slowly dropwise. After 10 min, 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 0.075 g, 0.252 mmol) was added, and the reaction was heated to 100° C. for 30 min. The mixture was cooled and partitioned between saturated aq. NH4Cl and DCM. The aq. layer was extracted with DCM (3×), and the combined organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The material was treated with DCM and purified by silica gel chromatography using 0-100% 90/10 DCM/MeOH in DCM The product-containing fractions were concentrated to afford 2-(2-(benzyloxy)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.018 g, 0.049 mmol, 19% yield) as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.76 (1H, br. s), 8.32 (1H, d, J=9.0 Hz), 8.00 (1H, dt, J=7.2, 1.0 Hz), 7.76 (1H, dt, J=7.9, 0.8 Hz), 7.26-7.59 (6H, m), 7.10-7.22 (2H, m), 6.87-6.99 (1H, m), 5.62 (2H, s), 3.36-3.51 (2H, m), 2.86 (2H, t, J=6.9 Hz). m/z (ESI, +ve) 370.0 (M+H)+.

Provenance & Evidence