5-Chloro-1-ethylindoline-2,3-dione → 5-Chloro-1-ethyl-3-hydroxy-3-((3-methoxypyridin-2-yl)methyl)indolin-2-one

HRID 1523052Notes

Reaction equation

HRID 1523052 reaction equation
BrC1C(CC2(O)C3C(=CC=C(C)C=3)N(CCC(C)C)C2=O)=NC=CC=1.[Cl:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH2:36][CH3:37])[C:31](=[O:38])[C:30]2=[O:39].[CH3:40][O:41][C:42]1[C:43]([CH3:48])=[N:44][CH:45]=[CH:46][CH:47]=1>>[Cl:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH2:36][CH3:37])[C:31](=[O:38])[C:30]2([OH:39])[CH2:48][C:43]1[C:42]([O:41][CH3:40])=[CH:47][CH:46]=[CH:45][N:44]=1

Participants

4

Reactant 3

HCID 29896025-Chloro-1-ethylindoline-2,3-dioneHCID 30152703-Methoxy-2-methylpyridineHCID 904186613-((3-Bromopyridin-2-yl)methyl)-3-hydroxy-1-isopentyl-5-methylindolin-2-one

Product 1

HCID 863003965-Chloro-1-ethyl-3-hydroxy-3-((3-methoxypyridin-2-yl)methyl)indolin-2-one

Procedure

This compound was prepared in an analogous manner to 3-((3-bromopyridin-2-yl)methyl)-3-hydroxy-1-isopentyl-5-methylindolin-2-one using 5-chloro-1-ethylindoline-2,3-dione and 3-methoxy-2-methylpyridine. 1H-NMR δ 8.21 (s, 1H), 7.5 (bs, OH), 7.26 (m, 3H), 6.99 (s, 1H), 6.78 (d, 1H), 3.77 (s, 3H), 3.76 (m, 2H), 3.45 (d, 1H), 3.19 (d, 1H), 1.27 (t, 3H). Calculated mass for C17H17ClN2O3, 332.09. Observed, 333.1 (M+1).

Sources & evidence

ORD record
ord-7c5fee8ac4b9497891786ed688f84bd1
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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