Trifluoroacetic acid → 3-(2-(4-Fluorophenyl)-3-(methylcarbamoyl)-6-(3,3,3-trifluoropropyl)furo[2,3-b]pyridin-5-yl)benzoic acid

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Reaction Steps

TFA (2.24 ml, 29.0 mmol) was added to a stirring solution of tert-butyl 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(3,3,3-trifluoropropyl)furo[2,3-b]pyridin-5-yl)benzoate (315 mg, 0.581 mmol) in dichloroethane (5.81 ml) at rt. The reaction was allowed to stir for 1 h at rt and then was concentrated to dryness azeotroping with toluene to give the expected product 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(3,3,3-trifluoropropyl)furo[2,3-b]pyridin-5-yl)benzoic acid (189 mg, 0.389 mmol, 67% yield) consistent by LCMS and NMR. LC-MS retention time: 2.89 min; m/z (MH+): 487. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 3u C18 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. 1H NMR (400 MHz, DMSO-d6) δ 13.16 (br. s, 1H), 8.55-8.47 (m, 1H), 8.10-8.02 (m, 3H), 8.00-7.96 (m, 2H), 7.74 (d, J=7.8 Hz, 1H), 7.69-7.62 (m, 1H), 7.42 (t, J=8.9 Hz, 2H), 3.05-2.96 (m, 2H), 2.85-2.70 (m, 5H).

Provenance & Evidence