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

HRID 1681186노트

반응식

HRID 1681186 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].CN(C)P(N(C)C)(N(C)C)=O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[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

6

반응물 3

HCID 12679HexamethylphosphoramideHCID 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-quinolinecarboxylate

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

2,6-Dimethyl-4-(trimethylstannyl)pyridine (part g (10.1 g) and 1.52 g dichlorobis(triphenylphosphine)-palladium was added to a stirred solution of 12.13 g ethyl 7-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (part f) and 10 ml hexamethylphosphoramide (HMPA) in 240 ml dioxane under nitrogen. The reaction mixture was heated under reflux for 24 hours, then cooled and partitioned between water and methylene dichloride. The organic extract was washed with sodium chloride solution, dried (magnesium sulfate) and concentrated to give 12.0 g ethyl 1-cyclopropyl-7-(2,6-dimethyl-4-pyridinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, m.p. 198°-200° C.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperaturecooled
  4. custompartitioned between water and methylene dichloride
  5. extractionThe organic extract
  6. washwas washed with sodium chloride solution
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-40bfc8d671914c829b49b6e58aa512f7
출처 데이터셋
uspto-grants-1992_12
특허 번호
US05169853

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