3-(3-Fluorobenzoyl)pyridine → (3-(4-(1H-Pyrazol-1-yl)benzyl)-2,4-dichloroquinolin-6-yl)(3-fluorophenyl)(pyridin-3-yl)methanol

HRID 926505Notes

Reaction equation

HRID 926505 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[N:21]1([C:26]2[CH:45]=[CH:44][C:29]([CH2:30][C:31]3[C:32]([Cl:43])=[N:33][C:34]4[C:39]([C:40]=3[Cl:41])=[CH:38][C:37](Br)=[CH:36][CH:35]=4)=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[N:22]1>>[N:21]1([C:26]2[CH:27]=[CH:28][C:29]([CH2:30][C:31]3[C:32]([Cl:43])=[N:33][C:34]4[C:39]([C:40]=3[Cl:41])=[CH:38][C:37]([C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[OH:9])=[CH:36][CH:35]=4)=[CH:44][CH:45]=2)[CH:25]=[CH:24][CH:23]=[N:22]1

Participants

4

Reactant 3

HCID 129300293-(3-Fluorobenzoyl)pyridine3×HCID 867155943-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloroquinoline2×HCID 178418339Butyllithium

Product 1

HCID 74220811(3-(4-(1H-Pyrazol-1-yl)benzyl)-2,4-dichloroquinolin-6-yl)(3-fluorophenyl)(pyridin-3-yl)methanol

Procedure

The title compound was prepared analogously to the method in Intermediate 37 using (3-fluorophenyl)(pyridin-3-yl)methanone (Intermediate 34: step b) in place of (4-chlorophenyl)(pyridin-3-yl)methanone, except that 1.2 equivalents of Intermediate 34: step b and 1.1 equivalents of n-BuLi were used relative to 3-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloroquinoline (Intermediate 3: step c).

Sources & evidence

ORD record
ord-12d2d999736f4fdbbbf4ec853a14fbc2
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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