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

HRID 916662Notes

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]

Participants

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

customas described by Clews et al., Synthesis (2001)
customSolvent is removed
additionwater (30 mL) is added
extractionthe mixture is extracted with methylene chloride
dry with materialOn drying (MgSO4)
customthe solvent is removed
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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