Triphenylphosphine → 2-Chloro-6-(1-ethoxyvinyl)-isonicotinic acid methyl ester

HRID 1436577Notes

Reaction equation

HRID 1436577 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6](Cl)[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Sn](CCCC)(CCCC)[C:37]([O:39][CH2:40][CH3:41])=[CH2:38])CCC>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.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[C:6]([C:37]([O:39][CH2:40][CH3:41])=[CH2:38])[N:7]=[C:8]([Cl:10])[CH:9]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 93237Methyl 2,6-dichloroisonicotinateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

Product 1

HCID 866150002-Chloro-6-(1-ethoxyvinyl)-isonicotinic acid methyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Add 2,6-dichloro-isonicotinic acid methyl ester, tetrakis(triphenylphosphine)palladium(0) (0.763 g, 0.66 mmol), triphenylphosphine (0.346 g, 1.32 mmol), tributyl(l-ethoxyvinyl)tin (5.0 g, 13.9 mmol) and toluene (30 mL), to a sealed flask flushed with nitrogen. Heat at 100° C. overnight and cool to room temperature. Filter the mixture through a filtering agent, concentrate and purify (silica gel chromatography eluting with 25:75 ethyl acetate:hexanes) to give the title compound (84%).

Workup

  1. customto a sealed flask flushed with nitrogen
  2. temperaturecool to room temperature
  3. filtrationFilter the mixture through a filtering agent
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography eluting with 25:75 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-70ebaa6b37dc4b54b6acf514aad3e50f
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…