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

HRID 1523069Notes

Reaction equation

C(N1C2C(=CC=CC=2)C(O)(CC(=O)C2C=CC=CN=2)C1=O)CCC.[CH3:25][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]([CH3:25])[CH:27]=3)[N:31]([CH2:35][CH2:36][CH3:37])[C:30]2=[O:38])=[CH:41]1

Participants

Reactant 3

HCID 128023-Acetylindole

HCID 29441601-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-one

HCID 3125288Sbb038754

Product 1

HCID 863006843-(2-(1H-indol-3-yl)-2-oxoethyl)-3-hydroxy-5-methyl-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-methyl-1-propylindoline-2,3-dione and commercially available 1-(1H-indol-3-yl)ethanone (purchased from Fisher Scientific). 1H-NMR δ 9.02 (bs, 1H), 8.36 (d, 1H), 7.71 (m, 1H), 7.40 (m, 1H), 7.30-7.26 (m, 3H), 7.09 (d, 1H), 6.73 (d, 1H), 5.66 (s, 1H), 3.64 (m, 2H), 3.50 (d, 1H), 3.24 (d, 1H), 2.26 (s, 3H) 1.72 (m, 2H), 0.96 (t, 3H). Calculated mass for C22H22N2O3, 362.16. Observed 385.1 (M+Na).

Sources & evidence

ORD record: ord-ce192a1977dd451f85e9b5373084d09b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079853B2

Reaction notes

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