Stannane, tributyl(1-ethoxyethenyl)- → HCID 90409536, compound

HRID 589024Notes

Reaction equation

HRID 589024 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:14]([O:16][CH2:17][CH3:18])=[CH2:15])CCC>CC#N.CCOC(C)=O.[Cu]I.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>[CH2:17]([O:16][C:14]([C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1)=[CH2:15])[CH3:18]

Participants

7

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 27831712-Bromo-5-fluoropyridine

Product 1

HCID 90409536HCID 90409536, compoundYield 119.6%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-5-fluoropyridine (200 mg, 1 mmol), tributyl(1-ethoxyvinyl)tin (500 mg, 1 mmol), copper(I) iodide (20 mg, 0.1 mmol) and bis(triphenylphosphine)palladium(II) chloride (50 mg, 0.07 mmol) in MeCN (5 mL) was heated to 80° C. for 30 h. The reaction mixture was allowed to cool to room temperature and was diluted with EtOAc, washed with 5% NH4OH, brine, dried over MgSO4, filtered and concentrated to give a crude oil. The product was purified by flash column chromatography on silica gel eluting with a hexane; EtOAc gradient (0-30%) to give 2-(1-ethoxyvinyl)-5-fluoropyridine as a clear oil (0.2 g, 90%). LCMS calc. for C9H11FNO (M+H)+: m/z=168.1. found: 168.2.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with 5% NH4OH, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude oil
  7. customThe product was purified by flash column chromatography on silica gel eluting with a hexane

Sources & evidence

ORD record
ord-c681da34bf1343168c427f83d8427ed5
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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