Pyridine → 2-[2,2′-Bipyridin]-6-yl-1H-benzimidazole

HRID 2373186Notes

Reaction equation

HRID 2373186 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[NH:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[N:3]=1.C([Sn](CCCC)CCCC)CCC.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>[Pd]>[N:12]1[C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[NH:9][C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=2)[N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 3032732TributylstannanylHCID 86600975HCID 86600975, compound

Product 1

HCID 113802632-[2,2′-Bipyridin]-6-yl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In Scheme 3, the starting material is 2-bromo-6-carboxyl pyridine 7. Addition of an ortho-substituted aniline derivative 2 using BOP chemistry generates 2-bromo-6-benzimidazolyl pyridine 8. A tributyl-tin activated pyridine 11 is added to 8 in the presence of a palladium catalyst to yield 2-benzimidazolyl-6-pyridyl pyridine 6.

Sources & evidence

ORD record
ord-ccfd67e56d6e419baad9f5de09183b58
Source dataset
uspto-grants-2008_12
Patent number
US07459457B2

Reaction notes

Loading…