Aluminium lithium hydride → (5-bromo-1H-indole-2-ylmethyl)-dimethyl amine

Temperature

-20 °C

5-Bromo-1H-indole-2-carboxylic acid dimethylamide (1.34 g, 5.00 mmol) was taken in anhydrous THF (50 mL) (suspension), and cooled to −20° C. A solution of lithium aluminium hydride (1.0 M solution in THF, 10.0 mL, 10.0 mmol) was added dropwise at −20° C. over a period of 15 minutes under nitrogen, and allowed to warm to 10° C.; stirring was continued at 10° C. for 1 hour. The reaction mixture was carefully quenched with aq. saturated ammonium chloride solution (10 mL). The reaction mixture was diluted with ethyl acetate (150 mL). The organic phase was separated, washed with water (100 mL), then brine (100 mL), and dried over anhydrous Na2SO4. Solvent was evaporated, to give (5-bromo-1H-indole-2-ylmethyl)-dimethyl amine as an off-white solid. Yield: 1.27 g (crude).

1. temperatureto warm to 10° C.
2. customThe reaction mixture was carefully quenched with aq. saturated ammonium chloride solution (10 mL)
3. additionThe reaction mixture was diluted with ethyl acetate (150 mL)
4. customThe organic phase was separated
5. washwashed with water (100 mL)
6. dry with materialbrine (100 mL), and dried over anhydrous Na2SO4
7. customSolvent was evaporated

ORD record

ord-914a0c79eb9f4570a5774f2078008e77

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238640B2