Dimethylformamide → 5-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridine-2-carbonitrile

HRID 2242222Notes

Reaction equation

HRID 2242222 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=3)[O:10][N:9]=2)=[CH:4][N:3]=1.[CH3:23][N:24](C=O)C>[Zn].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:19]([C:16]1[CH:17]=[CH:18][C:13]([C:11]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:23]#[N:24])=[N:3][CH:4]=3)[N:12]=2)=[CH:14][CH:15]=1)[CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 592042672-Chloro-5-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridine

Product 1

HCID 592042695-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridine-2-carbonitrileYield 59%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

A solution of 2-chloro-5-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridine (5.0 g, 16.0 mmol), zinc cyamide (1.13 g, 9.58 mmol), tetrakis(triphenylphosphine) palladium (0) (0.74 g, 0.64 mmol) and DMF (16 mL) was stirred at 80° C. for 24 hours. The reaction mixture was cooled to room temperature, quenched with H2O (10 mL), and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with H2O (2×100 mL) and brine (2×100 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica, 2:8 EtOAc:hexanes) provided the title compound (2.87 g, 59% yield) as a solid.

Workup

  1. customquenched with H2O (10 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic extracts were washed with H2O (2×100 mL) and brine (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (silica, 2:8 EtOAc:hexanes)

Sources & evidence

ORD record
ord-832d6ef60a364c43a5e03a85337a9214
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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