Benzyl Bromide → HCID 10613176, compound

HRID 2221217Notes

Reaction equation

HRID 2221217 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[Br:1])[CH:7]=[CH:8]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 24758Sodium hydride2×HCID 27570207-Bromoindole

Product 1

HCID 10613176HCID 10613176, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Benzyl-7-bromo-1H-indole was prepared from 7-bromo-1H-indole (0.500 g, 2.55 mmol), sodium hydride (0.285 g, 7.13 mmol of 60% dispersion on mineral oil), benzyl bromide (0.67 mL, 5.6 mmol) in DMF (5 mL). The reaction mixture was stirred for 1 hour after the addition of sodium hydride and for 1 hour after the addition of benzyl bromide. The compound was purified by flash chromatography (using hexane as an eluant) and dried at 60° C. for 30 minutes to yield a cream-colored solid (0.508 g, 70%), mp: 74-75° C. 1HNMR (300 MHz, DMSO-d6): δ 7.5-7.65 (m, 2H), 7.15-7.35 (m, 4H), 6.8-7.0 (m, 3H), 6.6 (s, 1H), and 5.8 ppm (s, 2H).

Workup

  1. customThe compound was purified by flash chromatography (
  2. customdried at 60° C. for 30 minutes

Sources & evidence

ORD record
ord-9ef8c67f1c504892a365bb8197427474
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

Loading…