Benzyl Bromide → 1-Benzyl-4-bromo-1H-indole

HRID 2221204Notes

Reaction equation

HRID 2221204 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]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:6]1[C:7]2[C:3](=[C:2]([Br:1])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 6764944-Bromoindole

Product 1

HCID 220329431-Benzyl-4-bromo-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Benzyl-4-bromo-1H-indole was prepared from 4-bromo-1H-indole (1.58 g, 8.06 mmol), sodium hydride (0.680 g of 60% dispersion in oil, 17.0 mmol), and benzyl bromide (2.0 mL, 17 mmol) in DMF (15 mL) according to the procedure described in Step 1 of Example 5. Purification by flash chromatography (Biotage apparatus) using hexane as an eluant yielded a light yellow oil (1.61 g, 70%). 1HNMR (300 MHz, DMSO-d6): δ 7.65 (d, 1H, J=3.8 Hz), 7.5 (d, 1H, J=7.7 Hz), 7.15-7.35 (m, 6H), 7.05 (t, 1H, J=7.7 Hz), 6.45 (d, 1H, J=3.1 Hz), and 5.6 ppm (s, 2H).

Workup

  1. customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record
ord-f4cdc0ee1289400eb3f144e19b89cfa7
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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