1-Tributylstannyl-3-methyl-but-3-en-1-ine → Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-(3-methyl-but-3-en-1-inyl)-4-oxo-3-quinolinecarboxylate

HRID 129420노트

반응식

HRID 129420 반응식
Br[C:2]1[C:3]([F:22])=[C:4]([F:21])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7]2=[O:20].C([Sn](CCCC)(CCCC)[C:28]#[C:29][C:30]([CH3:32])=[CH2:31])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>[CH:12]1([N:10]2[C:11]3[C:6](=[CH:5][C:4]([F:21])=[C:3]([F:22])[C:2]=3[C:28]#[C:29][C:30]([CH3:32])=[CH2:31])[C:7](=[O:20])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9]2)[CH2:14][CH2:13]1

참가 물질

5

반응물 2

HCID 110136791-Tributylstannyl-3-methyl-but-3-en-1-ineHCID 11046932Ethyl 8-bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

생성물 1

HCID 88439967Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-(3-methyl-but-3-en-1-inyl)-4-oxo-3-quinolinecarboxylate수율 80.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

1.86 g of ethyl 8-bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 2.8 g of 1-tributylstannyl-3-methyl-but-3-en-1-ine and 0.29 g of tetrakis(triphenylphosphine)palladium(0) are refluxed for 6 hours in 20 ml of absolute toluene under a nitrogen atmosphere. The reaction mixture is filtered under hot conditions and concentrated, and the residue is stirred with hexane. After filtration with suction and drying, 1.43 g of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-(3-methyl-but-3-en-1-inyl)-4-oxo-3-quinolinecarboxylate are obtained (80% of theory).

후처리

  1. filtrationThe reaction mixture is filtered under hot conditions
  2. concentrationconcentrated
  3. filtrationAfter filtration with suction
  4. customdrying

출처 및 근거

ORD 기록
ord-241b52a06cbd4bed88dcbe9bdaca1cb9
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468742

반응 노트

불러오는 중…