Potassium Phosphate, Tribasic → HCID 87416753, compound

Participants

Reaction Steps

To a vial containing ethyl 5-trifluoromethoxyindole-2-carboxylic acid (500 mg, 1.83 mmol) were added 4-iodobenzotrifluoride (323 mg, 2.20 mmol), potassium phosphate (815 mg, 3.84 mmol), copper iodide (17.5 mg, 0.092 mmol), and trans N,N′-dimethyl-1,2-cyclohexanediamine (0.058 mL, 0.37 mmol). The resulting mixture was purged with N2, and degassed toluene (2 mL) was added. The reaction mixture was capped, placed in a 110° C. bath, and was stirred for 18 h. Upon cooling to room temperature, the mixture was filtered and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30% then 30 to 100% EtOAc in hexanes) gave the title compound: LCMS A, tr=4.28 min, m/z 418.1 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.80 (d, J=8.5 Hz, 2H), 7.60 (s, 1H), 7.48 (s, 1H), 7.47 (d, J=8.5 Hz, 2H), 7.17 (dd, J=9.0, 1.5 Hz, 1H), 7.07 (d, J=9.0 Hz, 1H), 4.25 (q, J=7.0 Hz, 2H), 1.25 (t, J=7.0 Hz, 3H).

Provenance & Evidence