Trifluoroacetic acid → HCID 24801273, compound

Participants

Reaction Conditions

Reaction Steps

2-chloro-6-(((4-(4-fluorophenyl)-1-methylpiperidin-4-yl)methoxy)methyl)-4-(trifluoromethyl)pyridine (80 mg, 0.192 mmol), tetrakis(triphenylphsophine)palladium(O) (22.18 mg, 0.019 mmol), and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (72.3 mg, 0.576 mmol) were combined in tetrahydrofuran (1.5 mL). The reaction was then treated with potassium hydroxide (0.392 ml, 0.392 mmol) and heated to 100° C. for 2 hours. After cooling, the solution was diluted with ethyl acetate (25 mL), washed with water (10 mL) and brine (10 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified via preparatory HPLC to yield the desired product (30.23 mg, 0.076 mmol, 39.7%) as the TFA salt. 1H-NMR (CDCl3, 400 MHz) δ 10.02 (s, 1H), 8.09 (s, 1H), 7.93 (s, 1H). LC: Tr=1.920 min, HPLC Method 1. Mass spec.: 397.03 (MH)+.

Provenance & Evidence