Stannane, tributyl(1-ethoxyethenyl)- → HCID 86720755, compound

HRID 2167709Notes

Reaction equation

HRID 2167709 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:17]([O:19][CH2:20][CH3:21])=[CH2:18])CCC>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.CN(C)C=O>[CH2:20]([O:19][C:17]([C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:10][CH3:11])=[O:9])=[N:6][CH:7]=1)=[CH2:18])[CH3:21]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 592769911049025-94-6

Product 1

HCID 86720755HCID 86720755, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a N,N-dimethylformamide (3.0 mL) solution of 5-chloro-N-methylpyrazine-2-carboxamide (0.25 g), tributyl(1-ethoxyethenyl)stannane (0.53 ml) and bis(triphenylphosphine)palladium(II) dichloride (55 mg) were added, and the resultant was stirred at 100° C. for 3 hours. After standing to cool to room temperature, the reaction solution was concentrated under reduced pressure, followed by azeotropy with toluene. The obtained residue was purified by silica gel column chromatography (NH-type silica gel; hexane/ethyl acetate-gradient elution=70/30→40/60) to obtain the title compound (0.23 g) as a pale yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (NH-type silica gel; hexane/ethyl acetate-gradient elution=70/30→40/60)

Sources & evidence

ORD record
ord-626d3d97d4004ccd8350e5fbf2859202
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

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