HCID 67445967, compound → HCID 67447857, compound

HRID 2194878Notes

Reaction equation

HRID 2194878 reaction equation
[Br:1][C:2]1[C:3](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1>C1(C)C=CC=CC=1.CCOCC>[Br:1][C:2]1[C:3]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 67445967HCID 67445967, compound

Product 1

HCID 67447857HCID 67447857, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

To solution of ethyl (2E)-3-(5-bromo-2-methoxypyridin-4-yl)acrylate (1 eq.) from step 2 in Toluene (0.23M) at 110° C. was added benzenesulfonyl hydrazide (3 eq.). The reaction mixture was stirred at 110° C. for 3 h, cooled to room temperature and diluted with Et2O. The organic phase was washed with saturated NaOH (1N), brine, dried over MgSO4, filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 50% in 30 min) afforded the desired compound.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic phase was washed with saturated NaOH (1N), brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  7. washeluting with Hex/EtOAc (0 to 50% in 30 min)

Sources & evidence

ORD record
ord-b93482dafca949b6a4b677bba602ff96
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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