Diethyl Ether → HCID 59277534, compound

tert-Butyl lithium (16.7 mL, 28.3 mmol, 1.7 M in pentanes) was added to a dry ether (20 mL) solution of 5-bromo-3,6-dimethyl-1H-indole (1.27 g, 5.67 mmol) at −78° C. under Argon. The mixture was stirred at 0° C. for 30 min then cooled to −78° C. DMF (18 mL) was added and the mixture was stirred at 0° C. for 1 h. The reaction was quenched with cold, saturated NH4Cl solution at −78° C. The mixture was diluted with ether and hexane, washed with brine, dried and evaporated. Crystallization from a CH2Cl2/hexane mixture afforded the title compound (810 mg 82%). 1H NMR (300 MHz, CDCl3) 10.29 (s, 1H), 8.06 (s, 1H), 8.00 (s, br, 1H), 7.15 (1s, 1H), 6.97 (s, 1H), 2.76 (s, 3H), 2.36 (s, 3H).

1. temperaturethen cooled to −78° C
2. stirringthe mixture was stirred at 0° C. for 1 h
3. customThe reaction was quenched with cold, saturated NH4Cl solution at −78° C
4. additionThe mixture was diluted with ether and hexane
5. washwashed with brine
6. customdried
7. customevaporated
8. customCrystallization from a CH2Cl2/hexane mixture

ORD record

ord-1eda22c8b9d4491fb2ae198b6770d1e8

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2