Benzyl Bromide → 1-Benzyl-5-bromo-3-pentyl-2-phenyl-1H-indole

HRID 731088Notes

Reaction equation

HRID 731088 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:5]2[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:22]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[C:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[C:6]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 68813934HCID 68813934, compound

Product 1

HCID 688139541-Benzyl-5-bromo-3-pentyl-2-phenyl-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, 5-bromo-3-pentyl-2-phenyl-1H-indole (1.711 g, 5 mmol) was reacted with k-t-butoxide (0.589 g, 5.25 mmol) and benzyl bromide (0.901 g, 5.25 mmol) in DMF (15 ml) to give the product (1.285 g, 2.972 mmol, 59%) as a white solid, mp 98-101° C. 1H DMSO-d6) δ 0.75 (t, J=7.0 Hz, 3H), 1.11-1.19 (m, 4H), 1.46-1.52 (m, 2H), 2.60 (t, J=7.5 Hz, 2H), 5.25 (s, 2H), 6.77-6.78 (m, 2H), 7.13-7.22 (m, 4H), 7.32 (d, J=8.7 Hz, 1H), 7.34-7.36 (m, 2H), 7.42-7.49 (m, 3H), 7.75 (d, J=1.8 Hz, 1H); [ESI(+)], m/z 432/434 (M+H)+.

Sources & evidence

ORD record
ord-99801ca07d5d4a73826355f84df5927b
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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