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

HRID 1523049Notes

Reaction equation

HRID 1523049 reaction equation
Br[C:2]1[C:3]([CH2:8]C2(O)C3C(=CC=C(C)C=3)N(CCC(C)C)C2=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[C:31](=[O:44])[C:30]2=[O:45].CC1C=CC=CN=1>>[Cl:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[C:31](=[O:44])[C:30]2([OH:45])[CH2:8][C:3]1[CH:2]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 79752-MethylpyridineHCID 80716865-Chloro-1-(2-(piperidin-1-yl)ethyl)indoline-2,3-dioneHCID 904186613-((3-Bromopyridin-2-yl)methyl)-3-hydroxy-1-isopentyl-5-methylindolin-2-one

Product 1

HCID 863005395-Chloro-3-hydroxy-1-(2-(piperidin-1-yl)ethyl)-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-(2-(piperidin-1-yl)ethyl)indoline-2,3-dione and 2-methylpyridine (purchased from Fisher Scientific). 1H-NMR δ 8.61 (d, 1H), 7.70 (m, 2H), 7.32 (dd, 1H), 7.24 (dd, 1H), 7.10 (d, 1H), 6.82 (m, 2H), 3.87-3.75 (m, 2H), 3.33 (d, 1H), 3.11 (d, 1H), 2.62-2.47 (m, 6H), 1.57 (m, 4H), 1.45 (m, 2H). Calculated mass for C21H24ClN3O2, 385.16, observed, 386.1 (M+1).

Sources & evidence

ORD record
ord-938312129ace40968d6b53f20aaef52c
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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