3-Acetylindole → 3-(2-(1H-indol-3-yl)-2-oxoethyl)-3-hydroxy-1-isobutylindolin-2-one

HRID 1523065Notes

Reaction equation

HRID 1523065 reaction equation
C(N1C2C(=CC=CC=2)C(O)(CC(=O)C2C=CC=CN=2)C1=O)CCC.[CH2:25]([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31](=[O:38])[C:30]1=[O:39])[CH:26]([CH3:28])[CH3:27].[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:31]2([OH:38])[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:29]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:30]2=[O:39])=[CH:41]1

Participants

4

Reactant 3

HCID 128023-AcetylindoleHCID 23872331-(2-methylpropyl)-2,3-dihydro-1H-indole-2,3-dioneHCID 29441601-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-one

Product 1

HCID 904175473-(2-(1H-indol-3-yl)-2-oxoethyl)-3-hydroxy-1-isobutylindolin-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 1-isobutylindoline-2,3-dione and commercially available 1-(1H-indol-3-yl)ethanone (purchased from Fisher Scientific). 1H-NMR δ 8.87 (bs, NH), 8.38 (m, 1H), 7.72 (d, 3.1 Hz, 1H), 7.49 (dd, 1H), 7.47 (m, 1H) 7.30 (m, 3H), 7.01 (dd, 1H), 6.86 (d, 7.8, 1H), 3.51 (m, 3H), 3.24 (d, 1H), 2.16 (m, 1H) 0.98 (dd, 6H). Calculated mass for C22H22N2O3, 362.16. Observed 385.3 (M+Na).

Sources & evidence

ORD record
ord-6ffa21d4d33d49d888dd341da70444c3
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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