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

HRID 1989162Notes

Reaction equation

HRID 1989162 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.[Br:28][C:29]1[C:30](B(O)O)=[N:31][CH:32]=[CH:33][CH:34]=1.BrC1C=NC=C(Br)C=1>>[Br: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:26])([F:25])[F:27])=[CH:22][CH:23]=3)[CH:5]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[N:9]=2)[CH:32]=[N:31][CH:30]=1

Participants

4

Reactant 3

HCID 693693,5-DibromopyridineHCID 57468747Trifluoro-methanesulfonic acid 6-cyclopropyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl esterHCID 686929203-Bromo-pyridine-boronic acid

Product 1

HCID 686910535'-Bromo-6-cyclopropyl-4-(4-trifluoromethylphenyl)-[2,3']bipyridinyl

Procedure

The title compound was prepared from trifluoro-methanesulfonic acid 6-cyclopropyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl ester (example A.34) (2.0 g, 4.86 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) (1.079 g, 5.34 mmol) according to the general procedure IVb. Obtained as a white solid (1.55 g, 76%). MS (ISP) 419.1 [(M+H)+] and 421.0 [(M+2+H)+].

Sources & evidence

ORD record
ord-f0c005a826ba49d79279d50e76fc4295
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

Loading…