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Dimethylformamide → 3-(2-Cyanophenyl)-5-(2-pyridyl)-2-methoxypyridine

HRID 497819
Notes
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Reaction equation

HRID 497819 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9](Br)[C:10]([O:13][CH3:14])=[N:11][CH:12]=1.[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B1OC(C([O-])=O)C=CO1)#[N:17].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>C(OCC)(=O)C>[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:9]1[C:10]([O:13][CH3:14])=[N:11][CH:12]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:8]=1)#[N:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 223189615'-Bromo-6'-methoxy-2,3'-bipyridineHCID 865903732-(2-Cyanophenyl)-1,3,2-dioxaborinate

Product 1

HCID 223190893-(2-Cyanophenyl)-5-(2-pyridyl)-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
140 °C

Procedure

Tetrakistriphenylphosphine palladium (0.15 g) was added to a mixed solution of 0.50 g of 5-(2-pyridyl)-3-bromo-2-methoxypyridine, 0.42 g of 2-(2-cyanophenyl)-1,3,2-dioxaborinate, 0.82 g of cesium carbonate and 20 ml of dimethylformamide and the mixture was stirred at 140° C. in a nitrogen atmosphere for 5 hours. After cooling to room temperature, ethyl acetate was added thereto, the mixture was washed with water and a saturated saline solution and dried over magnesium sulfate. The solvent was concentrated in vacuo and the residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:3) to give 0.36 of the title compound as pale yellow powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe mixture was washed with water
  3. dry with materiala saturated saline solution and dried over magnesium sulfate
  4. concentrationThe solvent was concentrated in vacuo
  5. customthe residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-779340c2cb404a56839a031b0de81559
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06949571B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes