3,4-Dimethoxybenzyl bromide → 3-(3,4-Dimethoxybenzyl)-1-isopentyl-5-methyl-2-oxoindolin-3-yl benzoate

HRID 1523089Notes

Reaction equation

HRID 1523089 reaction equation
C(OC1([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26](OC)[CH:25]=2)C2C(=CC=C(C)C=2)N(CC)C1=O)(=O)C1C=CC=CC=1.[C:36]([O:44][CH:45]1[C:53]2[C:48](=[CH:49][CH:50]=[C:51]([CH3:54])[CH:52]=2)[N:47]([CH2:55][CH2:56][CH:57]([CH3:59])[CH3:58])[C:46]1=[O:60])(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.BrCC1C=CC(OC)=C(OC)C=1>>[C:36]([O:44][C:45]1([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=2)[C:53]2[C:48](=[CH:49][CH:50]=[C:51]([CH3:54])[CH:52]=2)[N:47]([CH2:55][CH2:56][CH:57]([CH3:58])[CH3:59])[C:46]1=[O:60])(=[O:43])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 3

HCID 109004583,4-Dimethoxybenzyl bromideHCID 863006811-Ethyl-5-methyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl benzoateHCID 904149791-Isopentyl-5-methyl-2-oxoindolin-3-yl benzoate

Product 1

HCID 904183263-(3,4-Dimethoxybenzyl)-1-isopentyl-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-isopentyl-5-methyl-2-oxoindolin-3-yl benzoate and 4-(bromomethyl)-1,2-dimethoxybenzene. 1H-NMR δ 8.06 (d, 2H), 7.57 (t, 1H), 7.43 (t, 2H), 7.08 (d, 1H), 6.93 (s, 1H), 6.67 (d, 1H), 6.60 (t, 2H), 6.36 (s, 1H), 3.82 (s, 3H), 3.64 (m, 4H), 3.46 (m, 2H), 3.26 (d, 1H), 2.27 (s, 3H), 1.50 (m, 1H), 1.26 (m, 2H) 0.92 (dd, 6H).

Sources & evidence

ORD record
ord-5109fafe4d124acfb484256ed4adc51d
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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