Benzyl Bromide → HCID 68814389, compound

HRID 731074Notes

Reaction equation

HRID 731074 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:17])=[C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:6]2.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([N:6]1[C:7]2[C:3](=[C:2]([Br:1])[CH:10]=[CH:9][CH:8]=2)[C:4]([CH3:17])=[C:5]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 68814161HCID 68814161, compound

Product 1

HCID 68814389HCID 68814389, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 3. Thus, 4-bromo-3-methyl-2-phenyl-1H-indole (1.467 g, 5.126 mmol) was reacted with k-t-butoxide (0.604 g, 5.383 mmol) and benzyl bromide (0.924 g, 5.383 mmol) in DMF (15 ml) to give the product (1.286 g, 3.651 mmol, 71%) as a colorless oil. 1H DMSO-d6) δ 2.40 (s, 3H), 5.27 (s, 2H), 6.79-6.81 (m, 2H), 6.98 (t, J=7.6 Hz, 1H), 7.15-7.21 (m, 3H), 7.23 (dd, J=0.8, 7.5 Hz, 1H), 7.36-7.38 (m, 3H), 7.43-7.53 (m, 3H); [ESI(+)], m/z 376/378 (M+H)+.

Sources & evidence

ORD record
ord-73619f5d55e84f828f6ce99a7697c737
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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