2-Methylpyridine → 5-Chloro-1-ethyl-3-hydroxy-3-(pyridin-2-ylmethyl)indolin-2-one

HRID 1523055Notes

Reaction equation

HRID 1523055 reaction equation
Br[C:2]1[C:3]([CH2:8][C:9]2([OH:25])[C:17]3[C:12](=[CH:13][CH:14]=[C:15](C)[CH:16]=3)[N:11]([CH2:19][CH2:20]C(C)C)[C:10]2=[O:24])=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:26]C1C=C2C(=CC=1)N(CC)C(=O)C2=O.CC1C=CC=CN=1>>[Cl:26][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:19][CH3:20])[C:10](=[O:24])[C:9]2([OH:25])[CH2:8][C:3]1[CH:2]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 79752-MethylpyridineHCID 29896025-Chloro-1-ethylindoline-2,3-dioneHCID 904186613-((3-Bromopyridin-2-yl)methyl)-3-hydroxy-1-isopentyl-5-methylindolin-2-one

Product 1

HCID 863003955-Chloro-1-ethyl-3-hydroxy-3-(pyridin-2-ylmethyl)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 2-methylpyridine (purchased from Fisher Scientific). 1H-NMR δ 8.60 (d, 1H), 7.65 (dd, 1H), 7.27 (m, 3H), 7.09 (d, 1H), 6.75 (m, 2H), 3.72 (m, 2H), 3.35 (d, 1H), 3.09 (d, 1H), 1.21 (t, 3H).

Sources & evidence

ORD record
ord-beec32e7d822436e9fd4c51e707bcfe4
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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