Allyltributylstannane → 6-Allylnicotinonitrile

HRID 1466045Notes

Reaction equation

HRID 1466045 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[CH2:10]([Sn](CCCC)(CCCC)CCCC)[CH:11]=[CH2:12]>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:12]([C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1)[CH:11]=[CH2:10]

Participants

6

Reactant 2

HCID 90628AllyltributylstannaneHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 107968686-Allylnicotinonitrile

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-chloropyridine-3-carbonitrile (7.0 g, 50 mmol), allyl tri-n-butyltin (18.2 g, 55.0 mmol) and Pd(PPh3)2Cl2 (1 g) in 80 mL DMF was stirred at 90° C. for 3 hours. The mixture was cooled down and diluted with 1 L of EtOAc, washed with water (100 mL×2) and brine (100 mL), then concentrated. The residue was purified by column chromatography (PE:EtOAc=10:1) to afford the title compound.

Workup

  1. temperatureThe mixture was cooled down
  2. washwashed with water (100 mL×2) and brine (100 mL)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-1b507b6e56c542159931d4fe6d571ed8
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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