Aluminium lithium hydride → HCID 58019920, compound

Participants

Reaction Conditions

Reaction Steps

In an 8 mL vial equipped with a stir bar was placed 5-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridine-2-carboxylic acid methyl ester (I-146, 100 mg, 0.259 mmol) and tetrahydrofuran (1.3 mL). The solution was cooled to 0° C. and then lithium aluminum hydride (39.3 mg, 1.04 mmol) was added resulting in strong gas evolution. Then mixture was stirred at 0° C. for 1 hour and then concentrated with a stream of nitrogen. The solid was diluted with dichloromethane (2 mL) and then slowly quenched with water (7 mL). The aqueous portion was extracted with DCM (3×6 mL), the organic portions were combined, filtered through Celite, dried (MgSO4) and concentrated. The crude material was purified by silica gel column chromatography utilizing 30% acetone/dichloromethane to produce 22 mg of P-599 as a pale orange viscous oil in 24% yield.

Provenance & Evidence