5-Chloro-1-propylindoline-2,3-dione → 5-Chloro-3-hydroxy-3-((5-methoxypyridin-2-yl)methyl)-1-propylindolin-2-one

HRID 1523050Notes

Reaction equation

HRID 1523050 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][CH3:38])[C:31](=[O:39])[C:30]2=[O:40].[CH3:41][O:42][C:43]1[CH:44]=[CH:45][C:46]([CH3:49])=[N:47][CH:48]=1>>[Cl:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH2:36][CH2:37][CH3:38])[C:31](=[O:39])[C:30]2([OH:40])[CH2:49][C:46]1[CH:45]=[CH:44][C:43]([O:42][CH3:41])=[CH:48][N:47]=1

Participants

4

Reactant 3

HCID 29882815-Chloro-1-propylindoline-2,3-dioneHCID 133587775-Methoxy-2-methylpyridineHCID 904186613-((3-Bromopyridin-2-yl)methyl)-3-hydroxy-1-isopentyl-5-methylindolin-2-one

Product 1

HCID 863005385-Chloro-3-hydroxy-3-((5-methoxypyridin-2-yl)methyl)-1-propylindolin-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-propylindoline-2,3-dione and 5-methoxy-2-methylpyridine. 1H-NMR δ 8.31 (s, 1H), 7.25 (m, 2H), 7.01 (d, 1H), 6.84 (s, 1H), 6.78 (m, 1H), 4.02 (bs, OH), 3.91 (s, 3H), 3.61 (m, 2H), 3.28 (d, 1H), 3.06 (d, 1H), 1.79 (m, 2H), 0.98 (t, 3H). Calculated mass for C18H19ClN2O3, 346.11. Observed, 347.1 (M+1).

Sources & evidence

ORD record
ord-1f705b4d4425422dbd97126dcd78f3aa
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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