p-Xylyl bromide → [5-(Benzyloxy)-1-(4-methylbenzyl)-1H-indol-2-yl]methyl acetate

HRID 2373489Notes

Reaction equation

HRID 2373489 reaction equation
[C:1]([O:4][CH2:5][C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:10][CH:9]=2)(=[O:3])[CH3:2].[CH3:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>>[C:1]([O:4][CH2:5][C:6]1[N:7]([CH2:23][C:24]2[CH:31]=[CH:30][C:27]([CH3:28])=[CH:26][CH:25]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:10][CH:9]=2)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 7721p-Xylyl bromideHCID 21964292[5-(Benzyloxy)-1H-indol-2-yl]methyl acetate

Product 1

HCID 21964286[5-(Benzyloxy)-1-(4-methylbenzyl)-1H-indol-2-yl]methyl acetate

Procedure

The title compound was prepared from [5-(benzyloxy)-1H-indol-2-yl]methyl acetate and 4-methylbenzyl bromide in substantially the same manner, as described in step 3 of Example 4. The product was obtained as a white solid. Mass-spectrum (ESI, [M+H)+) m/z 400. 1H NMR (300 MHz, DMSO-d6) δ 7.45 (d, 2H, J=8.34 Hz), 7.37 (t, 2H, J=7.19 Hz), 7.31 (d, 1H, J=7.30 Hz), 7.26 (d, 1H, J=7.56 Hz), 7.15 (d, 1H, J=2.44 Hz), 7.07 (d, 2H, J=8.76 Hz), 6.85 (d, 2H, J=8.81 Hz), 6.84 (s, 1H), 6.25 (s, 1H), 5.35 (s, 2H), 5.17 (s, 2H), 5.09 (s, 2H), 2.22 (s, 3H), 1.84 ppm (s, 3H).

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-7cffba69b473439d8e3a05ea05762927
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

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