1-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-one → 3-Hydroxy-1-isobutyl-3-(2-(6-methoxypyridin-2-yl)-2-oxoethyl)-5-methylindolin-2-one
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][C:34]([CH3:38])=[CH:35][CH:36]=2)[C:31](=[O:39])[C:30]1=[O:40])[CH:26]([CH3:28])[CH3:27].[CH3:41][O:42][C:43]1[N:48]=[C:47]([C:49](=[O:51])[CH3:50])[CH:46]=[CH:45][CH:44]=1>>[OH:39][C:31]1([CH2:50][C:49]([C:47]2[CH:46]=[CH:45][CH:44]=[C:43]([O:42][CH3:41])[N:48]=2)=[O:51])[C:32]2[C:37](=[CH:36][CH:35]=[C:34]([CH3:38])[CH:33]=2)[N:29]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:30]1=[O:40]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 using 1-isobutyl-5-methylindoline-2,3-dione and commercially available 1-(6-methoxypyridin-2-yl)ethanone (purchased from Fisher Scientific). 1H-NMR δ 7.70 (m, 2H), 7.19 (d, 1H), 7.10 (d, 1H), 6.97 (dd, 1H), 6.75 (d, 1H), 5.39 (s, OH), 4.02-3.98 (m, 4H), 3.56-3.42 (m, 3H), 2.30 (s, 3H), 2.16 (m, 1H), 0.97 (dd, 6H). calculated mass for C21H24N2O4, 368.17, observed, 391.1 (M+Na).
Sources & evidence
- ORD record
- ord-818c2ebd2e4c4b33be907d6b13dc858c
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079853B2
Reaction notes
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