Benzyl Bromide → 1,3-Dibenzyl-5-bromo-2-methyl-1H-indole

HRID 731053Notes

Reaction equation

HRID 731053 reaction equation
[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=2)[NH:10][C:9]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:9]1[CH3:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 688163193-Benzyl-5-bromo-2-methyl-1H-indole

Product 1

HCID 688151801,3-Dibenzyl-5-bromo-2-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 3. Thus, 3-benzyl-5-bromo-2-methyl-1H-indole (1.651 g, 5.5 mmol) was reacted with k-t-butoxide (0.648 g, 5.775 mmol) and benzyl bromide (0.991 g, 5.775 mmol) in DMF (20 ml) to give the product (1.842 g, 4.719 mmol, 86%) as a viscous brown oil. 1H NMR (DMSO-d6) δ 2.33 (s, 3H), 4.03 (s, 2H), 5.42 (s, 2H), 6.95 (d, J=7.3 Hz, 2H), 7.10-7.14 (m, 2H), 7.18-7.29 (m, 7H), 7.34 (d, J=8.7 Hz, 1H), 7.53 (d, J=1.8 Hz, 1H); [ESI(+)], m/z 390/392 (M+H)+.

Sources & evidence

ORD record
ord-08f3efa5412d451486175a7578a26adf
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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