3-Acetylindole → 3-(2-(1H-indol-3-yl)-2-oxoethyl)-5-chloro-3-hydroxy-1-propylindolin-2-one

HRID 1523076Notes

Reaction equation

HRID 1523076 reaction equation
C(N1C2C(=CC=CC=2)C(O)(CC(=O)C2C=CC=CN=2)C1=O)CCC.[Cl:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH2:35][CH2:36][CH3:37])[C:30](=[O:38])[C:29]2=[O:39].[NH:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([C:49](=[O:51])[CH3:50])=[CH:41]1>>[NH:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([C:49](=[O:51])[CH2:50][C:29]2([OH:39])[C:28]3[C:32](=[CH:33][CH:34]=[C:26]([Cl:25])[CH:27]=3)[N:31]([CH2:35][CH2:36][CH3:37])[C:30]2=[O:38])=[CH:41]1

Participants

4

Reactant 3

HCID 128023-AcetylindoleHCID 29441601-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-oneHCID 29882815-Chloro-1-propylindoline-2,3-dione

Product 1

HCID 863005443-(2-(1H-indol-3-yl)-2-oxoethyl)-5-chloro-3-hydroxy-1-propylindolin-2-one

Procedure

This compound was made in a similar manner to 1-butyl-3-hydroxy-3-(2-oxo-2-(pyridin-2-yl)ethyl)indolin-2-one using 5-chloro-1-propylindoline-2,3-dione and commercially available 1-(1H-indol-3-yl)ethanone (purchased from Fisher Scientific). 1H-NMR δ 8.71 (bs, NH) 8.38 (m, 1H), 7.79 (d, 1H), 7.49 (d, 1H), 7.41 (m, 1H), 7.35-7.31 (m, 2H), 7.26 (m, 1H), 6.78 (d, 1H), 5.00 (bs, OH), 3.65 (m, 2H), 3.50 (d, 1H), 3.25 (d, 1H), 1.69 (m, 2H), 0.96 (t, 3H). calculated mass for C21H19ClN2O3, 382.11, observed, 383.1 (M+1).

Sources & evidence

ORD record
ord-3d2738047f2040b680bb655430a4daab
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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