Aluminium lithium hydride → 5-bromo-2-pyrrolidin-1-ylmethyl-1H-indole

Temperature

0 °C

To a suspension of (5-bromo-1H-indol-2-yl)-pyrrolidin-1-yl-methanone (0.53 g, 1.8 mmol) in THF (50 mL) at 0° C. was slowly added lithium aluminum hydride (0.20 g, 5.4 mmol). The mixture was stirred under nitrogen at 0° C. for a while and the cooling bath was allowed to warm to room temperature. The mixture was then stirred at room temperature for 17 hours. The reaction was quenched by careful, successive, dropwise addition of water (0.2 mL), 15% NaOH aqueous solution (0.2 mL), and water (0.6 mL). The solid was filtered and washed with MeOH and CH2Cl2. The filtrate was concentrated to dryness, and dried under vacuum, to give 5-bromo-2-pyrrolidin-1-ylmethyl-1H-indole as a white solid. Yield: 0.45 g (90%).

1. temperatureto warm to room temperature
2. stirringThe mixture was then stirred at room temperature for 17 hours
3. customThe reaction was quenched by careful, successive,
4. additiondropwise addition of water (0.2 mL), 15% NaOH aqueous solution (0.2 mL), and water (0.6 mL)
5. filtrationThe solid was filtered
6. washwashed with MeOH and CH2Cl2
7. concentrationThe filtrate was concentrated to dryness
8. customdried under vacuum

ORD record

ord-86cf673281594b42bc32b56e1de6efda

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238640B2