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-isopropoxy-phenyl)-1H-quinolin-2-one

HRID 50173Notes

Reaction equation

HRID 50173 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][CH:21]([CH3:23])[CH3:22])[CH:15]=1.[Cl:24][C:25]1[N:30]=[CH:29][C:28]([C:31]([C:33]2[N:34]([CH3:38])[CH:35]=[N:36][CH:37]=2)=[O:32])=[CH:27][CH:26]=1>>[Cl:24][C:25]1[N:30]=[CH:29][C:28]([C:31]([OH:32])([C:33]2[N:34]([CH3:38])[CH:35]=[N:36][CH:37]=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][CH:21]([CH3:23])[CH3:22])[CH:15]=2)=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 120166732-Chloro-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridineHCID 224654236-Bromo4-(3-isopropoxy-phenyl)-2-methoxy-quinoline

Product 1

HCID 224654026-[(6-Chloro-pyridin-3-yl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-isopropoxy-phenyl)-1H-quinolin-2-one

Procedure

Following the same procedure as that described in example 1E, 6-bromo-4-(3-isopropoxy-phenyl)-2-methoxy-quinoline (238.4 mg, 0.640 mmol) and (6-chloro-pyridin-3-yl)-(3-methyl-3H-imidazol-4-yl)-methanone (156 mg, 0.705 mmol) generated the title compound of 34C (80 mg, 24% yield).

Sources & evidence

ORD record
ord-e16f4675167a47178c41e6d9b12e9cec
Source dataset
uspto-grants-2004_03
Patent number
US06710209B2

Reaction notes

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