Tetrabutylammonium Fluoride → HCID 45256865, compound

Participants

Reaction Conditions

Reaction Steps

TBAF (1M in THF) (0.5 mL, 0.5 mmol) was added to a solution of 5-[(6-chloro-5-(4-pyrrolidin-1-ylphenyl)-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. The mixture was diluted with EtOAc (10 mL) and washed with 2N HCl, followed by water and concentrated. Purification by reverse phase HPLC eluting with 10-90% MeCN:water) afforded the title compound as an off-white solid. LC-MS: calculated for C25H22ClN3O3 447.13, observed m/e 448.04 (M+H)+ (Rt 1.80 min). 1H NMR (500 MHz, CD3OD): δ 1H NMR (500 MHz, CD3OD): δ 7.87 (s, 1H) 7.48 (s, 1H) 7.42 (m, 2H) 7.28 (s, 1H) 7.22 (m, 2H) 6.75 (m, 2H) 3.84 (s, 3H) 3.31 (m, 2H) 2.61 (s, 3H) 2.03 (m, 2H).

Provenance & Evidence