(Z)-1-Ethoxy-2-(tributylstannyl)ethene → (E)-ethyl 6-(2-ethoxyvinyl)imidazo[1,2-a]pyridine-3-carboxylate

HRID 405828Notes

Reaction equation

HRID 405828 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:10]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)[CH:21]=[CH:22][O:23][CH2:24][CH3:25])CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:24]([O:23]/[CH:22]=[CH:21]/[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:10]=2)[CH:7]=1)[CH3:25]

Participants

5

Reactant 2

HCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 22031055Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 71281057(E)-ethyl 6-(2-ethoxyvinyl)imidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a stirring mixture of ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate (24s) (1 g, 3.72 mmol) and tetrakis(triphenylphosphine)palladium(0) (215 mg, 0.19 mmol) in anhydrous toluene (10 mL) under argon was added tributyl[2-ethoxyethenyl]stannane (1.7 g, 4.65 mmol). The reaction mixture was heated in a microwave sealed tube overnight at 90° C. The reaction was cooled to room temperature and was filtered through celite. The solvent was concentrated and the crude product was purified by silica chromatography to afford (E)-ethyl 6-(2-ethoxyvinyl)imidazo[1,2-a]pyridine-3-carboxylate (111). MS m/z 261.3 (M+1)+.

Workup

  1. temperatureThe reaction mixture was heated in a microwave
  2. customsealed tube overnight at 90° C
  3. filtrationwas filtered through celite
  4. concentrationThe solvent was concentrated
  5. customthe crude product was purified by silica chromatography

Sources & evidence

ORD record
ord-862b37a5353d49899180e593ffcac7ee
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

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