Potassium Cyanide → HCID 11998318, compound

HRID 908581Notes

Reaction equation

HRID 908581 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[N:9]=2)[N:3]=1.[C-:19]#[N:20].[K+].C([Sn](Cl)(CCCC)CCCC)CCC>C(#N)C.CCCCCCC.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:10]2[N:9]=[C:8]([C:4]3[N:3]=[C:2]([C:19]#[N:20])[CH:7]=[CH:6][CH:5]=3)[O:12][N:11]=2)[CH:14]=1

Participants

7

Reactant 3

HCID 9032Potassium CyanideHCID 15096Tributyltin ChlorideHCID 86637146HCID 86637146, compound

Product 1

HCID 11998318HCID 11998318, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6342AcetonitrileSolventHCID 8900HeptaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-6-(3-pyridin-3-yl-[1,2,4]oxadiazol-5-yl)-pyridine (250 mg, 0.83 mmol) and 80 mg of potassium cyanide (1.24 mmol) in 15 ml of acetonitrile was degassed three times (vacuum/nitrogene), added a solution of 24 μl Tributyltin chloride (1 μmol) in heptane, 2.3 mg of bis-(diphenylphosphino)ferrocene (4.1 μmol) and 4 mg of bispalladium tris(dibenzylidene acetone) (4.1 μmol) were added. The suspension was degassed three times and stirred at ambident temperature for 30 minutes. The mixture was degassed again and heated at 80° C. for 17 hours. The reaction mixture concentrated, residue was diluted with ethyl acetate and washed with water. The organic layer was dried with sodium sulphate, concentrated, and purified by column chromatography over silica gel using 20% ethyl acetate in petroleum ether, Yield 80 mg. Mp 201-203° C.

Workup

  1. additionwere added
  2. customThe suspension was degassed three times
  3. customThe mixture was degassed again
  4. concentrationThe reaction mixture concentrated
  5. additionresidue was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialThe organic layer was dried with sodium sulphate
  8. concentrationconcentrated
  9. custompurified by column chromatography over silica gel using 20% ethyl acetate in petroleum ether, Yield 80 mg

Sources & evidence

ORD record
ord-e5015aa5a6ba470081a7c22f30662580
Source dataset
uspto-grants-2011_09
Patent number
US08017631B2

Reaction notes

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