1-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-one → 5-Chloro-3-hydroxy-1-isobutyl-3-(2-(6-methoxypyridin-2-yl)-2-oxoethyl)indolin-2-one
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][CH:36]([CH3:38])[CH3:37])[C:30](=[O:39])[C:29]2=[O:40].[CH3:41][O:42][C:43]1[N:48]=[C:47]([C:49](=[O:51])[CH3:50])[CH:46]=[CH:45][CH:44]=1>>[Cl:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH2:35][CH:36]([CH3:37])[CH3:38])[C:30](=[O:39])[C:29]2([OH:40])[CH2:50][C:49]([C:47]1[CH:46]=[CH:45][CH:44]=[C:43]([O:42][CH3:41])[N:48]=1)=[O:51]Participants
4
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 from 5-chloro-1-isobutylindoline-2,3-dione and 1-(6-methoxypyridin-2-yl)ethanone (purchased from Fisher Scientific). 1H-NMR δ 7.75 (m, 1H), 7.67 (d, 1H), 7.35 (d, 1H), 7.29 (d, 1H), 7.00 (dd, 1H), 6.79 (d, 1H) 5.40 (bs, OH), 4.00 (m, 4H), 3.57-3.43 (m, 3H), 2.14 (m, 1H), 0.97 (dd, 6H). calculated mass for C20H21N2O4, 388.12, observed, 389.1 (M+1).
Sources & evidence
- ORD record
- ord-bd3512ea38d547709f0baa7b780aee04
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079853B2
Reaction notes
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