HCID 90203845, compound → HCID 90203632, compound

HRID 1480282Notes

Reaction equation

HRID 1480282 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH:9]2[CH2:11][CH2:10]2)=[CH:4][N:3]=1.[C:12]([Zn]C#N)#[N:13]>CN(C=O)C.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].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]>[Cl:8][C:6]1[C:5]([CH:9]2[CH2:11][CH2:10]2)=[CH:4][N:3]=[C:2]([C:12]#[N:13])[CH:7]=1

Participants

6

Reactant 2

HCID 90203845HCID 90203845, compoundHCID 178514179HCID 178514179, compound

Product 1

HCID 90203632HCID 90203632, compoundYield 73.2%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred solution of 2,4-dichloro-5-cyclopropylpyridine (example 215a, 2.2 g, 11.76 mmol) in DMF (10 ml) was purged with argon for 10 minutes. To this reaction mixture was added dicyanozinc (926 mg, 7.65 mmol) followed by addition of DPPF (520 mg, 1.02 mmol) and Pd2dba3 (535 mg, 0.58 mmol). The reaction mixture was again purged with argon for 10 minutes. The reaction mixture was then stirred at 100° C. for 1 hour. The catalyst was filtered off on a pad of celite and the filtrate was diluted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and evaporated down to dryness. The obtained crude material was purified by flash chromatography on silica eluting with a gradient of heptane and ethyl acetate to yield the title compound (1 g, 50%) as off white crystalline solid. MS (ESI, m/z): 179.2 (M+H+).

Workup

  1. customThe reaction mixture was again purged with argon for 10 minutes
  2. filtrationThe catalyst was filtered off on a pad of celite
  3. additionthe filtrate was diluted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated down to dryness
  7. customThe obtained crude material
  8. customwas purified by flash chromatography on silica eluting with a gradient of heptane and ethyl acetate

Sources & evidence

ORD record
ord-1ec5f9ad26c74cf8a36aa084f8d37536
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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