HCID 90406336, compound → HCID 81689841, compound

Participants

Reaction Conditions

Reaction Steps

BH3-Me2S (0.43 g, 5.8 mmol) was added dropwise to a solution of ketonitrile (13) (0.5 g, 1.9 mmol) in THF (50 mL). The reaction mixture was heated at 65° C. under reflux for 18 h. After completion of the reaction (as monitored by TLC) the reaction mixture was quenched by MeOH (15 mL) and stirred at rt for an additional 1 h. The reaction mixture was concentrated and purification by column chromatography (100-200 silica mesh, 4-6% MeOH in DCM) gave Example 2 as a pale yellow semi-solid. Yield (0.48 g, 96%); 1H NMR (400 MHz, DMSO-d6) δ 7.80 (bs, 3H), 7.24 (t, J=8.0 Hz, 1H), 6.89-6.87 (m, 2H), 6.82-6.80 (m, 1H), 5.54 (bs, 1H), 4.65 (bs, 1H), 3.87 (dd, J=11.4, 2.8 Hz, 2H), 3.81 (d, J=6.4 Hz, 2H), 3.37-3.30 (m, 2H), 2.87-2.79 (m, 2H), 2.02-1.96 (m, 1H), 1.88-1.80 (m, 2H), 1.69-1.65 (m, 2H), 1.34-1.27 (m, 2H); RP HPLC: tR=3.89 min, 95% (AUC); ESI MS m/z 266.27 [M+H]+.

Provenance & Evidence