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

HRID 1989168Notes

Reaction equation

HRID 1989168 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10](I)[CH:9]=2)=[CH:4][CH:3]=1.[Br:16][C:17]1[C:18](B(O)O)=[N:19][CH:20]=[CH:21][CH:22]=1.BrC1C=NC=C(Br)C=1>>[Br:16][C:17]1[CH:22]=[C:21]([C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:13]=[C:12]([CH3:14])[N:11]=2)[CH:20]=[N:19][CH:18]=1

Participants

4

Reactant 3

HCID 693693,5-DibromopyridineHCID 574686424-(4-Chloro-phenyl)-2-iodo-6-methyl-pyridineHCID 686929203-Bromo-pyridine-boronic acid

Product 1

HCID 686930645'-Bromo-4-(4-chloro-phenyl)-6-methyl-[2,3']bipyridinyl

Procedure

The title compound was prepared from 4-(4-chloro-phenyl)-2-iodo-6-methyl-pyridine (example A.29) (2.15 g, 6.5 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) (1.448 g, 7.1 mmol) according to the general procedure IVb. Obtained as a white solid (1.35 g, 57%). MS (ISP) 358.9 [(M+H)+], 360.9 [(M+2+H)+] and 363.0 [(M+4+H)+].

Sources & evidence

ORD record
ord-5f8c4a1a9b334b71b0af7f77f679f852
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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