3-Acetylindole → 3-(2-(1H-indol-3-yl)-2-oxoethyl)-3-hydroxy-1-isopentyl-5-methylindolin-2-one

HRID 1523060Notes

Reaction equation

HRID 1523060 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][C:35]([CH3:39])=[CH:36][CH:37]=2)[C:32](=[O:40])[C:31]1=[O:41])[CH2:26][CH:27]([CH3:29])[CH3:28].[NH:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]([C:51](=[O:53])[CH3:52])=[CH:43]1>>[NH:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]([C:51](=[O:53])[CH2:52][C:32]2([OH:40])[C:33]3[C:38](=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=3)[N:30]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:31]2=[O:41])=[CH:43]1

Participants

4

Reactant 3

HCID 128023-AcetylindoleHCID 29441601-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-oneHCID 47302421-Isopentyl-5-methylindoline-2,3-dione

Product 1

HCID 904160893-(2-(1H-indol-3-yl)-2-oxoethyl)-3-hydroxy-1-isopentyl-5-methylindolin-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-isopentyl-5-methylindoline-2,3-dione and commercially available 1-(1H-indol-3-yl)ethanone (purchased from Fisher Scientific). 1H-NMR δ 9.21 (bs, NH), 8.34 (m, 1H), 7.67 (d, 1H), 7.38 (m, 1H), 7.30-7.23 (m, 3H), 7.08 (d, 1H), 6.73 (d, 1H) 5.74 (bs, 1H), 3.68 (t, 2H), 3.49 (d, 1H), 3.21 (d, 1H), 2.27 (s, 3H), 1.67-1.49 (m, 3H), 0.95 (dd, 6H).

Sources & evidence

ORD record
ord-fe6810f33d56438a9be66489c6ba0720
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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