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Water → 2-(1H-imidazol-2-yl)-nicotinonitrile

HRID 916662
Notes
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Reaction equation

HRID 916662 reaction equation
Br[C:2]1[C:3]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.BrC1[C:15](C#N)=[N:16]C=CC=1.O>CN(C=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[NH:12]1[CH:11]=[CH:10][N:9]=[C:8]1[C:3]1[N:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:15]#[N:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 962WaterHCID 8176943-Bromopyridine-2-carbonitrileHCID 575033123-bromo-2-(1H-imidazol-2-yl)-pyridine

Product 1

HCID 552537712-(1H-imidazol-2-yl)-nicotinonitrile

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-bromo-2-(1H-imidazol-2-yl)-pyridine (prepared from 3-bromo-pyridine-2-carbonitrile essentially as described by Clews et al., Synthesis (2001):1549) (675 mg, 3 mmol), zinc cyanide (223 mg, 1.9 mmol), Pd2(dba)3 (137 mg, 0.15 mmol), DPPF (160 mg, 0.3 mmol) and water (0.2 mL) in DMF (15 mL) is degassed with argon for 15 minutes. The mixture is then heated at 40° C. overnight in a sealed tube. Solvent is removed, water (30 mL) is added and the mixture is extracted with methylene chloride. On drying (MgSO4), the solvent is removed and the resulting solid is washed with ether (5×10 mL) to give the product (170).

Workup

  1. customas described by Clews et al., Synthesis (2001)
  2. customSolvent is removed
  3. additionwater (30 mL) is added
  4. extractionthe mixture is extracted with methylene chloride
  5. dry with materialOn drying (MgSO4)
  6. customthe solvent is removed
  7. washthe resulting solid is washed with ether (5×10 mL)

Sources & evidence

ORD record
ord-76d790e1bb5149248da43bf9ab610072
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07271170B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes