Cesium carbonate → 9-Fluoro-6-phenanthridinamine

HRID 1097140

반응식

HRID 1097140 반응식
Cl[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B1OC(C)(C)C(C)(C)O1.C1C2CC3(N)CC(C2)CC1C3.Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)Cl.O.O1CCOCC1>[F:10][C:8]1[CH:7]=[CH:6][C:3]2[C:2]([CH:9]=1)=[C:13]1[C:12]([CH:17]=[CH:16][CH:15]=[CH:14]1)=[N:11][C:4]=2[NH2:5]

참가 물질

9

반응물 4

HCID 10796Cesium carbonateHCID 64150Amantadine HydrochlorideHCID 1090002-Chloro-4-fluorobenzonitrileHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

생성물 1

HCID 112528289-Fluoro-6-phenanthridinamine수율 3,082.6%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 2-chloro-4-fluorobenzonitrile (1.0 g, 6.42 mmol), 2-aminophenylboronic acid pinacol ester (1.6 g, 7.1 mmol), palladium(II) acetate (0.07 g, 0.32 mmol), amantadine hydrochloride (0.24 g, 1.3 mmol) and cesium carbonate (4.6 g, 14.1 mmol) were added to dioxane previously deaerated with nitrogen and heated to reflux for 17 hours. After cooling, both distilled water and methylene chloride (50 mL) were added to the reaction mixture. The solvent layer was separated and concentrated to give a crude oil that was purified by column chromatography by first using 1:1 ethyl acetate and hexanes ratio followed by 4:1 ethyl acetate/hexanes as the eluants. The pure product was collected to give 9-fluoro-6-phenanthridinamine (42 g, 32% Yield) whose NMR spectrum is consistent with the proposed structure.

후처리

  1. temperatureheated
  2. temperatureto reflux for 17 hours
  3. temperatureAfter cooling
  4. customThe solvent layer was separated
  5. concentrationconcentrated
  6. customto give a crude oil that
  7. customwas purified by column chromatography
  8. customThe pure product was collected

출처 및 근거

ORD 기록
ord-4cdd18daebdb4a86a7f28e216dde29c9
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08142909B2

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