3-Bromo-2-chloropyridine → HCID 58548585, compound

HRID 1846775Notes

Reaction equation

HRID 1846775 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1.[Br:17][C:18]1[C:19](Cl)=[N:20][CH:21]=[CH:22][CH:23]=1.C(O[Na])(C)(C)C>CS(C)=O>[Br:17][C:18]1[C:19]([O:16][CH:13]2[CH2:14][CH2:15][CH:10]([C:2]3[NH:3][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[N:1]=3)[CH2:11][CH2:12]2)=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6933243-Bromo-2-chloropyridineHCID 58548667HCID 58548667, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 58548585HCID 58548585, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 4-(1H-benzoimidazol-2-yl)-cyclohexanol (0.36 g, 1.67 mmol), 3-bromo-2-chloro-pyridine (0.64 g, 3.34 mmol), t-BuONa (0.37 g, 3.34 mmol) and DMSO (5 mL) was heated at 60° C. for 2 days under N2 atmosphere. Then the mixture was concentrated under vacuum and the obtained residue was purified by silica gel chromatograph (DCM:MeOH=10:1) to give 2-[4-(3-bromo-pyridin-2-yloxy)-cyclohexyl]-1H-benzoimidazole (0.15 g, 0.403 mmol, 36% yield) as white solid.

Workup

  1. concentrationThen the mixture was concentrated under vacuum
  2. customthe obtained residue was purified by silica gel chromatograph (DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-e4ab30a87d4d4168bdad84a549b733e8
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

Loading…