Tetrabutylammonium Fluoride → HCID 45256864, compound

Participants

Reaction Conditions

Reaction Steps

TBAF (1M in THF) (0.5 mL) was added to a solution of 5-[(6-chloro-5-(2-fluoro-4-methoxyphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoic acid in dioxane (3 mL). The reaction was heated at 80° C. for 16 h. Volatiles were removed and the residue acidified with 2N aqueous HCl and extracted with EtOAc. The organic phase was washed with water and concentrated. Purification by reverse phase HPLC eluting with 15-90% MeCN:water afforded the title compound as a white solid. LC-MS: calculated for C27H36ClFN2O4 426.08, observed m/e 427.00 (M+H)+ (Rt 1.90 min). 1 H NMR (500 MHz, CD3OD): δ 7.87 (s, 1H) 7.48 (s, 1H) 7.42 (m, 2H) 7.28 (s, 1H) 7.20 (m, 1 H) 6.80 (dd, 1H) 6.75 (dd, 1H) 3.84 (s, 3H) 2.61 (s, 3H).

Provenance & Evidence