3,5-Dibromopyridine → 5'-Bromo-6-methyl-4-(4-trifluoromethylphenyl)-[2,3']bipyridinyl

HRID 1989161Notes

Reaction equation

HRID 1989161 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.[Br:26][C:27]1[C:28](B(O)O)=[N:29][CH:30]=[CH:31][CH:32]=1.BrC1C=NC=C(Br)C=1>>[Br: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]=[N:29][CH:28]=1

Participants

4

Reactant 3

HCID 693693,5-DibromopyridineHCID 57468647Trifluoro-methanesulfonic acid 6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl esterHCID 686929203-Bromo-pyridine-boronic acid

Product 1

HCID 686924845'-Bromo-6-methyl-4-(4-trifluoromethylphenyl)-[2,3']bipyridinyl

Procedure

The title compound was prepared from trifluoro-methanesulfonic acid 6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl ester (example A.32) (2.0 g, 5.2 mmol) and commercially available 3-bromo-pyridine-boronic acid [CAS-No. 452972-09-07] (alternatively prepared from commercially available 3,5-dibromopyridine according to Tetrahedron 2002, 58(17), 3323 or Synthesis 2003, (7), 1035) (1.152 g, 5.7 mmol) according to the general procedure IVb. Obtained as a white solid (1.70 g, 83%). MS (ISP) 393.0 [(M+H)+] and 395.0 [(M+2+H)+].

Sources & evidence

ORD record
ord-72d7138799db4073b758deadf478747a
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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