Ethyl 7-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate → Ethyl 1-cyclopropyl-7-(2,6-dimethyl-4-pyridinyl)6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 1957486노트

반응식

HRID 1957486 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([Sn](C)(C)C)[CH:5]=[C:4]([CH3:12])[N:3]=1.Br[C:14]1[CH:23]=[C:22]2[C:17]([C:18](=[O:32])[C:19]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:20][N:21]2[CH:24]2[CH2:26][CH2:25]2)=[CH:16][C:15]=1[F:33]>O1CCOCC1.O>[CH:24]1([N:21]2[C:22]3[C:17](=[CH:16][C:15]([F:33])=[C:14]([C:6]4[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([CH3:12])[CH:5]=4)[CH:23]=3)[C:18](=[O:32])[C:19]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:20]2)[CH2:25][CH2:26]1

참가 물질

5

반응물 2

HCID 10405837Ethyl 7-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateHCID 129132682,6-Dimethyl-4-(trimethyl-stannyl)pyridine

생성물 1

HCID 9999813Ethyl 1-cyclopropyl-7-(2,6-dimethyl-4-pyridinyl)6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate수율 72.1%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매2회

실험 절차

2,6-dimethyl-4-(trimethylstannyl)pyridine (2.6 g) in dioxane (6 ml) is slowly dropped into a stirred mixture of ethyl 7-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (3.1 g), dioxane (55 ml) and hexamethylenphosphoramide (2.6 ml) kept under argon. To the stirred mixture, dichlorobis (triphenylphosphine) palladium (0.4 g) is added. The reaction mixture is heated under reflux for 24 hours. After cooling it is poured in water (200 ml) and repeatedly extracted with dichloromethane. The organic extracts are dried and evaporated to dryness. The residue, after trituration with ethyl ether, gives ethyl 1-cyclopropyl-7-(2,6-dimethyl-4-pyridinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (2.4 g) m.p. 196°-199° C.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter cooling it
  4. extractionrepeatedly extracted with dichloromethane
  5. customThe organic extracts are dried
  6. customevaporated to dryness

출처 및 근거

ORD 기록
ord-0c6b2a3cec6e425085ef52c359d70e96
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05786350

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