Potassium Phosphate, Tribasic → HCID 22660562, compound

Participants

Reaction Steps

A suspension of (5-Bromo-1H-indol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (Example 3, 0.057 g) in dry toluene (0.5 mL) was treated with Pd(OH)2 (0.001 g) under N2 atmosphere. The resulting mixture was then treated with 3-methoxyphenylboronic acid (0.057 g) and then K3PO4 (0.12 g), and heated at 95° C. for 24 h. The reaction mixture was cooled to ambient temperature and diluted with water (2 mL) and toluene (10 mL). The organic layer was separated and washed with brine (2 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography (0-12% methanol/dichloromethane) to give the title compound (0.005 g). 1H NMR (400 MHz, CDCl3): δ 9.96 (br s, 1H), 7.53 (d, J=1.6 Hz, 1H), 7.51 (d, J=1.6 Hz, 1H), 7.35 (t, J=7.9 Hz, 1H), 7.23 (s, 1H), 7.21 (s, 1H), 7.17 (m, 1H), 6.87 (dd, J=2.2, 8.1 Hz, 1H), 6.82 (d, J=1.8 Hz, 1H), 3.99 (br s, 4H), 3.86 (s, 3H), 2.52 (t, J=4.9 Hz, 4H), 2.35 (s, 3H). MS (electrospray): exact mass calculated for C21H23N3O2, 349.18; m/z found, 350.2 [M+H]+.

Provenance & Evidence