2-Chloro-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridine → 6-[(6-Chloro-Pyridin-3-yl)-Hydroxy-(3-Methyl-3H-Imidazol-4-yl)-Methyl]-4-(3-Ethoxy-Phenyl)-1H-Quinolin-2-One

HRID 1384353Notes

Reaction equation

HRID 1384353 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12]C)[CH:6]=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=1.[Cl:23][C:24]1[N:29]=[CH:28][C:27]([C:30]([C:32]2[N:33]([CH3:37])[CH:34]=[N:35][CH:36]=2)=[O:31])=[CH:26][CH:25]=1>>[Cl:23][C:24]1[N:29]=[CH:28][C:27]([C:30]([OH:31])([C:32]2[N:33]([CH3:37])[CH:34]=[N:35][CH:36]=2)[C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH:6]=[C:5]3[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=2)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 120166732-Chloro-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridineHCID 224654196-Bromo4-(3-ethoxy-phenyl)-2-methoxy-quinoline

Product 1

HCID 224653976-[(6-Chloro-Pyridin-3-yl)-Hydroxy-(3-Methyl-3H-Imidazol-4-yl)-Methyl]-4-(3-Ethoxy-Phenyl)-1H-Quinolin-2-One

Procedure

Following the same procedure as that described in example 1E, 6-bromo-4-(3-ethoxy-phenyl)-2-methoxy-quinoline (2 g, 5.59 mmol) and (6-chloro-pyridin-3-yl)-(3-methyl-3H-imidazol-4-yl)-methanone (1.48 g, 6.70 mmol) generated the title compound of 26A (1.458 g, 52% yield).

Sources & evidence

ORD record
ord-db194a535ac2482f892594e2c5627bd6
Source dataset
uspto-grants-2001_07
Patent number
US06258824B1

Reaction notes

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