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

HRID 1523088Notes

Reaction equation

HRID 1523088 reaction equation
[C:1]([O:9][C:10]1([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)[C:18]2[C:13](=[CH:14][CH:15]=[C:16](C)[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:36](OC1C2C(=CC=CC=2)N(CCC(C)C)C1=O)(=O)[C:37]1C=CC=C[CH:38]=1.BrCC1C=CC(OC)=C(OC)C=1>>[C:1]([O:9][C:10]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:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:20][CH2:21][CH:37]([CH3:38])[CH3:36])[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 109004583,4-Dimethoxybenzyl bromideHCID 863006811-Ethyl-5-methyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl benzoateHCID 904174431-Isopentyl-2-oxoindolin-3-yl benzoate

Product 1

HCID 863009723-(3,4-Dimethoxybenzyl)-1-isopentyl-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-2-oxoindolin-3-yl benzoate and 4-(bromomethyl)-1,2-dimethoxybenzene. 1H-NMR δ 8.06 (d, 2H), 7.55 (t, 1H), 7.43 (t, 2H), 7.29 (t, 1H), 7.13 (d, 1H), 7.01 (t, 1H), 6.69 (t, 2H), 6.61 (d, 1H) 6.34 (s, 1H), 3.82 (s, 3H) 3.63 (m, 4H), 3.49 (m, 2H), 3.28 (d, 1H), 1.51 (m, 1H), 1.51 (q, 2H), 0.92 (dd, 6H). Calculated mass for C29H31NO5, 473.22. Observed 496.2 (M+Na).

Sources & evidence

ORD record
ord-0b37260f9dd8434a85598fff11d35ddd
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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