1-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-one → 5-Chloro-3-hydroxy-3-(2-(6-methoxypyridin-2-yl)-2-oxoethyl)-1-(2-(piperidin-1-yl)ethyl)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][CH2:36][N:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)[C:30](=[O:43])[C:29]2=[O:44].[CH3:45][O:46][C:47]1[N:52]=[C:51]([C:53](=[O:55])[CH3:54])[CH:50]=[CH:49][CH:48]=1>>[Cl:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)[C:30](=[O:43])[C:29]2([OH:44])[CH2:54][C:53]([C:51]1[CH:50]=[CH:49][CH:48]=[C:47]([O:46][CH3:45])[N:52]=1)=[O:55]Participants
4
Reactant 3
Product 1
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-chloro-1-(2-(piperidin-1-yl)ethyl)indoline-2,3-dione and 1-(6-methoxypyridin-2-yl)ethanone (commercially available from Fisher Scientific). 1H-NMR δ 7.72 (t, 1H), 7.63 (d, 1H), 7.34 (d, 1H), 7.28 (d, 1H) 6.98 (d, 1H), 6.86 (d, 1H), 5.5 (bs, OH), 4.04 (d, 1H), 4.00 (s, 3H), 3.8 (m, 2H), 3.60 (d, 1H), 2.60 (m, 6H), 1.55 (m, 4H), 1.43 (m, 2H). calculated mass for C23H26ClN3O4, 443.16, observed, 444.1 (M+1).
Sources & evidence
- ORD record
- ord-a0bdf471be544fcdaff4471e6e15ef0a
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079853B2
Reaction notes
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