2-Chloro-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridine → [4-(3,5-dichloro-phenyl)-2-methoxy-quinolin-6-yl]-(6-chloro-pyridin-3-yl)-(3-methyl-3H-imidazol-4-yl)-methanol

HRID 50157Notes

Reaction equation

HRID 50157 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:13])[CH:6]=[C:5]2[C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=1.[Cl:22][C:23]1[N:28]=[CH:27][C:26]([C:29]([C:31]2[N:32]([CH3:36])[CH:33]=[N:34][CH:35]=2)=[O:30])=[CH:25][CH:24]=1>>[Cl:21][C:16]1[CH:15]=[C:14]([C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:29]([C:26]4[CH:27]=[N:28][C:23]([Cl:22])=[CH:24][CH:25]=4)([C:31]4[N:32]([CH3:36])[CH:33]=[N:34][CH:35]=4)[OH:30])[CH:3]=3)[N:8]=[C:7]([O:12][CH3:13])[CH:6]=2)[CH:19]=[C:18]([Cl:20])[CH:17]=1

Participants

3

Reactant 2

HCID 120166732-Chloro-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridineHCID 224654106-Bromo-4-(3,5-dichloro-phenyl)-2-methoxy-quinoline

Product 1

HCID 22465439[4-(3,5-dichloro-phenyl)-2-methoxy-quinolin-6-yl]-(6-chloro-pyridin-3-yl)-(3-methyl-3H-imidazol-4-yl)-methanolYield 39.5%

Procedure

Following the same procedure as described in example 1E, 6-bromo-4-(3,5-dichloro-phenyl)-2-methoxy-quinoline (1.88 g, 4.91 mmol) and (6-chloro-pyridin-3-yl)-(3-methyl-3H-imidazol-4-yl)-methanone (0.94 g, 4.27 mmol) generated the title compound of 16C as a yellow solid (0.885 g, 39.5% yield).

Sources & evidence

ORD record
ord-8918c891693143f7b5f9de5a8c5ab229
Source dataset
uspto-grants-2004_03
Patent number
US06710209B2

Reaction notes

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