Sodium hydride → HCID 67339147, compound

Participants

Reaction Steps

A 20 mL scintillation vial equipped with a septum cap and a magnetic stirring bar was charged under N2 with NaH (12.0 mg, 60% suspension in mineral oil, 0.30 mmol). A solution of hydroxyacetic acid methyl ester (54.0 mg, 0.60 mmol) in THF (1.0 mL) was added dropwise to the vial. Immediately after the addition was complete, a solution of {4-[2-methanesulfonyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-5-ylethynyl]-phenyl}-methanol (compound 47-1, 49.1 mg, 0.100 mmol) in THF (1 mL) was added. The resulting yellowish suspension was stirred at it for 5 min, then diluted with ACN (2 mL) and quenched by addition of water (2 mL). The resulting solution was stirred at it for 5 min, then an additional 15 min at 65° C. The solution was acidified with 5% aqueous HCl and extracted with EtOAc (three times, 3 mL). The organic layers were combined and washed with 5% aqueous HCl and water and evaporated to dryness in vacuo to give the crude product as yellowish solid. LR-MS (APT-ES): mixture of two N-SEM isomers, calculated for C24H27ClN2O5Si 486.2, observed m/e 487.0 (M+H)+ (Rt 3.09, 3.20 min). The crude product was used in the next step without further purification.

Provenance & Evidence