Benzyl Bromide → HCID 68814191, compound

HRID 731102Notes

Reaction equation

HRID 731102 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[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH2:24]([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[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 68814532HCID 68814532, compound

Product 1

HCID 68814191HCID 68814191, compound

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-phenyl-1H-indole (1.811 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 (20 ml) to give the product (1.932 g, 4.271 mmol, 85%) as a white solid, mp 155-157° C. 1H NMR (DMSO-d6) δ 3.99 (s, 2H), 5.32 (s, 2H), 6.82 (d, J=7.2 Hz, 2H), 7.07 (d, J=7.3 Hz, 2H), 7.09-7.23 (m, 7H), 7.34-7.39 (m, 3H), 7.43-7.49 (m, 3H), 7.53 (d, J=1.8 Hz, 1H); [ESI(+)], m/z 453/455 (M+H)+.

Sources & evidence

ORD record
ord-674f6a08873746629ec4bb2803a4994d
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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