Tetrabutylammonium Fluoride → HCID 45102606, compound

Participants

Reaction Conditions

Reaction Steps

TBAF (1 M in THF) (0.63 mL, 0.63 mmol) was added to a solution of methyl 5-[(6-fluoro-5-(2′-hydroxybiphenyl-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate (75 mg, 0.125 mmol) in THF (10 mL). The reaction was heated at 80° C. for 6 h. Volatiles were removed and the residue was purified by HPLC eluting with 20-80% MeCN:water. The resulting white solid was dissolved in MeOH (3 mL) and water (2 mL). Aqueous 5 M NaOH (250 μl) was added. The solution was heated at 70° C. for 30 min. Volatiles were removed and the residue was re-dissolved in 10 mL water and extracted with ethyl acetate to afford the title compound as a white solid product. LC/MS: calculated for C27H19FN2O4 454.45, observed m/e 455(M+H)+ (1.97/4 min). 1H-NMR (500 MHz, D6-acetone): 8.02-6.98 (13H, m), 2.62 (3H, s).

Provenance & Evidence