5-chloro-1-(2-phenylethyl)-1H-indole-2,3-dione → 5-Chloro-3-hydroxy-3-((3-methoxypyridin-2-yl)methyl)-1-phenethylindolin-2-one

HRID 1523048Notes

Reaction equation

HRID 1523048 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][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:31](=[O:44])[C:30]2=[O:45].[CH3:46][O:47][C:48]1[C:49]([CH3:54])=[N:50][CH:51]=[CH:52][CH:53]=1>>[Cl:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:31](=[O:44])[C:30]2([OH:45])[CH2:54][C:49]1[C:48]([O:47][CH3:46])=[CH:53][CH:52]=[CH:51][N:50]=1

Participants

4

Reactant 3

HCID 29300415-chloro-1-(2-phenylethyl)-1H-indole-2,3-dioneHCID 30152703-Methoxy-2-methylpyridineHCID 904186613-((3-Bromopyridin-2-yl)methyl)-3-hydroxy-1-isopentyl-5-methylindolin-2-one

Product 1

HCID 863003985-Chloro-3-hydroxy-3-((3-methoxypyridin-2-yl)methyl)-1-phenethylindolin-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-phenethylindoline-2,3-dione and 3-methoxy-2-methylpyridine. 1H-NMR δ 8.21 (dd, 1H), 7.33-7.17 (m, 8H), 6.95 (d, 1H), 6.62 (d, 1H), 5.5 (bs, OH), 3.98 (m, 1H), 3.86 (m, 1H), 3.78 (s, 3H), 3.37 (d, 1H), 3.09 (d, 1H), 2.96 (t, 2H).

Sources & evidence

ORD record
ord-9c9983739c894e7caaf4cccdf1b342ec
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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