3,5-Dimethoxybenzyl Bromide → 3-(3,5-Dimethoxybenzyl)-1-ethyl-5-methyl-2-oxoindolin-3-yl benzoate

HRID 1523083Notes

Reaction equation

HRID 1523083 reaction equation
[C:1]([O:9][C:10]1([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[C:27](OC)=[C:26]([O:34][CH3:35])[CH:25]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N:12]([CH2:20][CH3:21])[C:11]1=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C2C(=CC=C(C)C=2)N(CC)C1=O)(=O)C1C=CC=CC=1.COC1C=C(C=C(OC)C=1)CBr>>[C:1]([O:9][C:10]1([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:34][CH3:35])[CH:25]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N:12]([CH2:20][CH3:21])[C:11]1=[O:22])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 12744903,5-Dimethoxybenzyl BromideHCID 863006811-Ethyl-5-methyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl benzoateHCID 904159121-Ethyl-5-methyl-2-oxoindolin-3-yl benzoate

Product 1

HCID 863011223-(3,5-Dimethoxybenzyl)-1-ethyl-5-methyl-2-oxoindolin-3-yl benzoate

Procedure

This compound was made in an analogous fashion to 1-ethyl-5-methyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl benzoate using 1-ethyl-5-methyl-2-oxoindolin-3-yl benzoate and 3,5-dimethoxy benzyl bromide (purchased from Fisher Scientific). 1H NMR δ 8.08 (d, 2H), 7.60 (t, 1H), 7.57 (t, 2H), 7.10 (d, 1H), 6.90 (s, 1H), 6.65 (d, 1H), 6.33 (s, 1H), 6.18 (s, 2H), 3.79 (m, 1H), 3.62 (s, 6H), 3.59 (m, 1H), 3.52 (d, 1H), 3.22 (d, 1H), 2.28 (s, 3H), 1.07 (t, 3H).

Sources & evidence

ORD record
ord-3805f6d930f04e299e8e34610ffe3e27
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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