2-Chloro-4-iodopyridine → 2'-Chloro-6-methyl-4-(4-trifluoromethylphenyl)-[2,4']bipyridinyl

HRID 1989165Notes

Reaction equation

HRID 1989165 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[CH:3]=1.[Cl:26][C:27]1[CH:32]=[C:31](I)[CH:30]=[CH:29][N:28]=1>C([Mg]Cl)(C)C.[Cl-].[Cl-].[Zn+2]>[Cl:26][C:27]1[CH:32]=[C:31]([C:6]2[CH:5]=[C:4]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:20][CH:21]=3)[CH:3]=[C:2]([CH3:1])[N:7]=2)[CH:30]=[CH:29][N:28]=1

Participants

4

Reactant 2

HCID 15165112-Chloro-4-iodopyridineHCID 57468647Trifluoro-methanesulfonic acid 6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl ester

Product 1

HCID 866154422'-Chloro-6-methyl-4-(4-trifluoromethylphenyl)-[2,4']bipyridinyl

Reagents, catalysts & solvents 1

HCID 178461731HCID 178461731, compoundCatalyst

Procedure

The title compound was prepared from trifluoro-methanesulfonic acid 6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl ester (example A.32) (3.0 g, 7.8 mmol), commercially available 2-chloro-4-iodo-pyridine [CAS No. 153034-86-7] (1.92 g, 8.0 mmol) and i-PrMgCl/ZnCl2 according to the general procedure IVc protocol a. Obtained as a white solid (1.50 g, 55%). MS (ISP) 349.2 [(M+H)+] and 351 [(M+2+H)+].

Sources & evidence

ORD record
ord-ee745377a37441208e3e204e3ff1826c
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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