Water → 2-Bromo-3-(dipyridin-3-ylmethoxy)pyridine

HRID 1661134Notes

Reaction equation

HRID 1661134 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH:10]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Br:1][C:2]1[C:7]([O:8][CH:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 230702-Bromo-3-pyridinolHCID 574257823,3'-(Chloromethylene)dipyridine

Product 1

HCID 576132562-Bromo-3-(dipyridin-3-ylmethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 2-bromo-3-hydroxypyridine (0.90 g, 5.18 mmol) and 3-[chloro(pyridin-3-yl)methyl]pyridine (2-1) (0.82 g, 3.99 mmol) in DMF (10 mL) at 0° C. was added Cs2CO3 (1.95 g, 5.98 mmol). The mixture was stirred overnight, poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layer was dried, filtered, and concentrated to give a solid. The solid was purified by silica gel chromatography (3% MeOH in CH2Cl2) to give 2-bromo-3-(dipyridin-3-ylmethoxy)pyridine (2-2). LRMS m/z (M+H) Calcd: 343.2, found: 343.0.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. customThe combined organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a solid
  6. customThe solid was purified by silica gel chromatography (3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9926dbd939b74adfb5a08835fcf60abe
Source dataset
uspto-grants-2011_10
Patent number
US08030332B2

Reaction notes

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