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

Temperature

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., 1H), 7.56 (s, 1H), 7.42 (d, J=8.1 Hz, 2H), 7.24 (s, 1H), 6.98 (d, J=8.1 Hz, 2H), 6.55 (br. s., 1H), 3.88 (s, 3H).

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 record

ord-e467d2c0950a404ab4c41d395f033230

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889730B2