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

HRID 964021
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HRID 964021 반응식
[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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 1140Toluene용매2회

실험 절차

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##

후처리

  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%

출처 및 근거

ORD 기록
ord-5fe8bde37bb8469ca019fe63f36fcfec
출처 데이터셋
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05767128

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