3,4-Dimethoxybenzyl bromide → 3-(3,4-Dimethoxybenzyl)-5-methyl-2-oxo-1-propylindolin-3-yl benzoate

HRID 1523090Notes

Reaction equation

HRID 1523090 reaction equation
[C:1]([O:9][C:10]1([CH2:23][C:24]2[CH:29]=[C:28](OC)[C:27]([O:32][CH3:33])=[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:36](OC1C2C(=CC=C(C)C=2)N(CCC)C1=O)(=O)C1C=CC=CC=1.BrCC1C=CC(OC)=C(OC)C=1>>[C:1]([O:9][C:10]1([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:32][CH3:33])=[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][CH2:21][CH3:36])[C:11]1=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 904174755-Methyl-2-oxo-1-propylindolin-3-yl benzoate

Product 1

HCID 863009703-(3,4-Dimethoxybenzyl)-5-methyl-2-oxo-1-propylindolin-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 5-methyl-2-oxo-1-propylindolin-3-yl benzoate and 4-(bromomethyl)-1,2-dimethoxybenzene. 1H-NMR δ 8.06 (d, 2H), 7.57 (t, 1H), 7.43 (t, 2H), 7.07 (d, 1H), 6.90 (s, 1H), 6.68 (d, 1H) 6.62 (m, 2H), 6.39 (s, 1H), 3.83 (s, 3H), 3.66 (s, 3H), 3.56 (m, 1H) 3.47 (m, 2H), 3.25 (d, 1H), 2.27 (s, 3H), 1.52 (m, 2H), 0.84 (t, 3H). Calculated mass for C28H29NO5, 459.53. Observed 482.2 (M+Na).

Sources & evidence

ORD record
ord-2a6fff07cf8242b8a1d5f05f94c1719a
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

Loading…