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

HRID 1523066Notes

Reaction equation

HRID 1523066 reaction equation
C(N1C2C(=CC=CC=2)C(O)(CC(=O)C2C=CC=CN=2)C1=O)CCC.[CH2:25]([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[C:31]1=[O:40])[CH2:26][CH:27]([CH3:29])[CH3:28].[NH:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43]([C:50](=[O:52])[CH3:51])=[CH:42]1>>[NH:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43]([C:50](=[O:52])[CH2:51][C:32]2([OH:39])[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:30]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:31]2=[O:40])=[CH:42]1

Participants

4

Reactant 3

HCID 128023-AcetylindoleHCID 23625931-(3-methylbutyl)-1H-indole-2,3-dioneHCID 29441601-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-one

Product 1

HCID 863002413-(2-(1H-indol-3-yl)-2-oxoethyl)-3-hydroxy-1-isopentylindolin-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-isopentylindoline-2,3-dione and commercially available 1-(1H-indol-3-yl)ethanone (purchased from Fisher Scientific). 1H-NMR δ 9.41 (bs, 1H), 8.33 (s, 1H), 7.82 (m, 1H), 7.66 (d, 1H), 7.47 (d, 1H), 7.25 (m, 3H), 7.00 (t, 1H), 6.84 (d, 1H), 5.89 (bs, 1H), 3.71 (t, 2H), 3.49 (d, 1H), 3.21 (d, 1H), 1.62 (m, 2H), 1.54 (m, 1H), 0.94 (dd, 6H).

Sources & evidence

ORD record
ord-205d913f4fa54ddb85f990247197774a
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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