1-(Bromomethyl)-4-(1,1-dimethylethyl)benzene → [5-(Benzyloxy)-1-(4-tert-butylbenzyl)-1H-indol-2-yl]methyl acetate

HRID 2373492Notes

Reaction equation

HRID 2373492 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].[C:23]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]>>[C:1]([O:4][CH2:5][C:6]1[N:7]([CH2:31][C:30]2[CH:33]=[CH:34][C:27]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:28][CH:29]=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 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 21964292[5-(Benzyloxy)-1H-indol-2-yl]methyl acetate

Product 1

HCID 21964282[5-(Benzyloxy)-1-(4-tert-butylbenzyl)-1H-indol-2-yl]methyl acetate

Procedure

The title compound was prepared from [5-(benzyloxy)-1H-indol-2-yl]methyl acetate and 4-tert-butylbenzyl bromide in substantially the same manner, as described in step 3 of Example 4. The product was obtained as a white solid; mp: 132-133° C. Mass spectrum (ESI, [M+H]+) m/z 442. 1H NMR (400MHz, DMSO-d6) δ 7.45 (d, 2H, J=7.33 Hz), 7.38 (t, 2H, J=7.33 Hz), 7.32-7.27 (m, 4H), 7.16 (d, 1H, J=2.30 Hz), 6.88-6.84 (m, 3H), 6.53 (s, 1H), 5.36 (s, 2H), 5.18 (s, 2H), 5.08 (s, 2H), 1.77 (s, 3H), and 1.21 ppm (s, 9H).

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-a0946dc3a3044fb993d018bde2927a0b
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

Loading…