Sodium Hydroxide → 4-(1-Ethyl-5-trifluoromethanesulfonyl-1H-benzoimidazol-2-yl)-benzoic acid

Participants

Reaction Steps

4-(1-Ethyl-5-trifluoromethanesulfonyl-1H-benzoimidazol-2-yl)-benzoic acid methyl ester (152 mg, 0.368 mmol) was dissolved in warm ethanol (7 mL) and 1 M sodium hydroxide (1.0 mL) was added. The reaction mixture was heated to near reflux and stirred for 3 h. The reaction mixture was then partially evaporated by blowing with a stream of nitrogen and transferred to a vial containing EtOAc and 1 M aqueous hydrochloric acid. The organic phase was separated, washed with saturated brine, dried (Na2SO4) and evaporated to yield the acid 36: 1HNMR (400 MHz, d6-DMSO) δ 8.47 (d, J=1.55 Hz, 1H), 8.18 (d, J=8.66 Hz, 1H), 8.15 (d, J=8.81 Hz, 2H), 8.01 (dd, J=7.17, 1.17 Hz, 1H), 7.95 (d, J=8.25 Hz, 2H), 4.45 (q, J=7.11 Hz, 2H), 1.37 (t, J=7.09 Hz, 3H); LCMS-APCI m/z 397 [M−1]−.

Provenance & Evidence