Lithium Chloride → 2h-Pyrrolo[2,3-b]pyridin-2-one,5-acetyl-1,3-dihydro-1,3,3-trimethyl-

HRID 964021Notes

Reaction equation

HRID 964021 reaction equation
[Cl-].[Li+].[CH3:3][N:4]1[C:8]2=[N:9][CH:10]=[C:11](Br)[CH:12]=[C:7]2[C:6]([CH3:15])([CH3:14])[C:5]1=[O:16].[CH2:17]([O:19]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:18]>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>[CH3:3][N:4]1[C:8]2=[N:9][CH:10]=[C:11]([C:17](=[O:19])[CH3:18])[CH:12]=[C:7]2[C:6]([CH3:15])([CH3:14])[C:5]1=[O:16]

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 107534875-Bromo-1,3,3-trimethyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one

Product 1

HCID 106088542h-Pyrrolo[2,3-b]pyridin-2-one,5-acetyl-1,3-dihydro-1,3,3-trimethyl-Yield 90%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

Under argon, suspend 482 mg (11.37 mmol) of lithium chloride and 90 mg (7.84×10-5 mol) of tetrakis(triphenylphosphine)palladium in 10 ml of anhydrous toluene. Add to that suspension a solution of 1 g (3.92 mmol) of 1,3-dihydro-1,3,3-trimethyl-5-bromo-2H-pyrrolo[2,3-b]pyridin-2-one and 1.46 mg (4.04 mmol) of (1-ethoxyvinyl)tributyltin in 20 ml of anhydrous toluene. After 5 hours at reflux, evaporate off the solvent and take up the residue in a 1:1 mixture (30 ml) of dioxane and 10% hydrochloric acid. After 30 minutes' stirring at room temperature, evaporate off the dioxane. Filter off the resulting tin salts over Celite. Extract the filtrate with dichloromethane and dry over magnesium sulfate. After purification on a silica column, 780 mg of the title product are obtained in a yield of 90% ##STR59##

Workup

  1. temperatureAfter 5 hours at reflux
  2. customevaporate off the solvent
  3. customevaporate off the dioxane
  4. filtrationFilter off the resulting tin salts over Celite
  5. extractionExtract the filtrate with dichloromethane
  6. dry with materialdry over magnesium sulfate
  7. customAfter purification on a silica column, 780 mg of the title product
  8. customare obtained in a yield of 90%

Sources & evidence

ORD record
ord-5fe8bde37bb8469ca019fe63f36fcfec
Source dataset
uspto-grants-1998_06
Patent number
US05767128

Reaction notes

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