Sodium Carbonate → 6-Chloro-5-(4-methoxyphenyl)-1H-indole

Temperatur

90 °C

A mixture of 5-bromo-6-chloro-1H-indole (3.20 g, 13.9 mmol), sodium carbonate (3.68 g, 34.7 mmol), and 4-methoxyphenylboronic acid (2.41 g, 15.9 mmol) in EtOH (18 mL), toluene (18 mL) and water (18 mL) was degassed with N2 for 15 minutes, treated with tetrakis(triphenylphosphine)palladium(0) (1.20 g, 0.99 mmol) and heated to 90° C. for 23 hours. The cooled reaction mixture was poured into half-saturated NH4Cl solution (200 mL) and extracted with dichloromethane (3×120 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The resulting dark solid was purified by flash chromatography (5-20% EtOAc/heptane) to give the title compound (1.40 g, 39%) as a white solid. MS (ES+) 258.5 (M+H)+. 1H NMR (500 MHz, CDCl3) δ 8.16 (br. s., 1 H), 7.56 (s, 1 H), 7.42 (d, J=8.1 Hz, 2 H), 7.24 (s, 1 H), 6.98 (d, J=8.1 Hz, 2 H), 6.55 (br. s., 1 H), 3.88 (s, 3 H).

1. customwas degassed with N2 for 15 minutes
2. customThe cooled reaction mixture
3. extractionextracted with dichloromethane (3×120 mL)
4. dry with materialThe combined organic layers were dried over Na2SO4
5. concentrationconcentrated in vacuo
6. customThe resulting dark solid was purified by flash chromatography (5-20% EtOAc/heptane)

ORD-Eintrag

ord-257bba41205045a39d04387a345818cb

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09394285B2