Benzyl Bromide → HCID 68816825, compound

HRID 731067Notes

Reaction equation

HRID 731067 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:17])=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[C:6]([CH3:17])=[C:7]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 12395368HCID 12395368, compound

Product 1

HCID 68816825HCID 68816825, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 3. Thus, 6-bromo-3-methyl-2-phenyl-1H-indole (1.284 g, 4.489 mmol) was reacted with k-t-butoxide (0.529 g, 4.711 mmol) and benzyl bromide (0.809 g, 4.711 mmol) in DMF (10 ml) to give the product (1.440 g, 3.827 mmol, 85%) as a white solid, mp 97-101° C. 1H NMR (DMSO-d6)δ 2.20 (s, 3H), 5.32 (s, 2H), 6.79-6.80 (m, 2H), 7.14-7.21 (m, 4H), 7.36-7.39 (m, 2H), 7.43 (t, J=7.2 Hz, 1H), 7.48 (t, J=6.9 Hz, 2H), 7.53 (d, J=8.4 Hz, 1H), 7.60 (d, J=1.7 Hz, 1H); [ESI(+)], m/z 376/378 (M+H)+.

Sources & evidence

ORD record
ord-fe59a26b27de44ad98e8d9bbcca06a6b
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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