3-Oxocyclobutane-1-carbonitrile → 3-(2-(5-Bromo-2-methoxypyridin-3-yl)-2-oxoethylidene)cyclobutanecarbonitrile

HRID 1039682Notes

Reaction equation

HRID 1039682 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[C:10](/[O-:18])=[CH:11]/P(OC)(OC)=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[Li+].O=[C:21]1[CH2:24][CH:23]([C:25]#[N:26])[CH2:22]1>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[O:18])[CH:11]=[C:21]2[CH2:24][CH:23]([C:25]#[N:26])[CH2:22]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 130823903-Oxocyclobutane-1-carbonitrileHCID 59468662lithium (Z)-1-(5-bromo-2-methoxypyridin-3-yl)-2-(dimethoxyphosphoryl)ethenolate

Product 1

HCID 575158633-(2-(5-Bromo-2-methoxypyridin-3-yl)-2-oxoethylidene)cyclobutanecarbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of lithium (Z)-1-(5-bromo-2-methoxypyridin-3-yl)-2-(dimethoxyphosphoryl)ethenolate (2.0 g, 5.8 mmol) and 3-oxocyclobutanecarbonitrile (1.1 g, 12 mmol) in p-dioxane (6 ml) was heated at 120° C. by Microwave in 1 h. The mixture was cooled, taken up in H2O, extracted with EtOAc (3×), dried over MgSO4, concentrated to provide the title compound. MS (m+1): 307.0.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (3×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-110bc69582e74d318d23ee121b37e579
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Reaction notes

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