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

HRID 1927889Notes

Reaction equation

HRID 1927889 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[C:6]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[CH:5]=2)[CH2:3][CH2:2]1.[Cl:28][C:29]1[CH:34]=[C:33](I)[CH:32]=[CH:31][N:30]=1>C([Mg]Cl)(C)C.[Cl-].[Cl-].[Zn+2]>[Cl:28][C:29]1[CH:34]=[C:33]([C:8]2[CH:7]=[C:6]([C:18]3[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=3)[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[N:9]=2)[CH:32]=[CH:31][N:30]=1

Participants

4

Reactant 2

HCID 15165112-Chloro-4-iodopyridineHCID 57468747Trifluoro-methanesulfonic acid 6-cyclopropyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl ester

Product 1

HCID 866154432'-Chloro-6-cyclopropyl-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-cyclopropyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl ester (example A.34) (2.7 g, 7.0 mmol), commercially available 2-chloro-4-iodo-pyridine [CAS No. 153034-86-7] (1.62 g, 6.8 mmol) and i-PrMgCl/ZnCl2 according to the general procedure IVc protocol a. Obtained as a white solid (0.75 g, 30%). MS (ISP) 375.2 [(M+H)+] and 377.1 [(M+2+H)+].

Sources & evidence

ORD record
ord-a5da387aaab24e90bb8089ff63aa4fd5
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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