5-Fluoro-o-toluidine → 1-(4-fluoro-2-methylphenyl)-N-(5-fluoro-2-methylphenyl)phthalazin-6-amine

HRID 454867

반응식

HRID 454867 반응식
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH3:19])=[N:7][N:6]=[CH:5]2.[F:20][C:21]1[CH:22]=[CH:23][C:24]([CH3:28])=[C:25]([CH:27]=1)[NH2:26].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:8]2[C:9]3[C:4](=[CH:3][C:2]([NH:26][C:25]4[CH:27]=[C:21]([F:20])[CH:22]=[CH:23][C:24]=4[CH3:28])=[CH:11][CH:10]=3)[CH:5]=[N:6][N:7]=2)=[C:13]([CH3:19])[CH:14]=1

참가 물질

8

반응물 4

HCID 677745-Fluoro-o-toluidineHCID 21081571Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphineHCID 23676156Sodium t-butoxideHCID 667396776-Chloro-1-(4-fluoro-2-methylphenyl)phthalazine

생성물 1

HCID 452801281-(4-fluoro-2-methylphenyl)-N-(5-fluoro-2-methylphenyl)phthalazin-6-amine

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 887Methanol용매2회HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A mixture of 6-chloro-1-(4-fluoro-2-methylphenyl)phthalazine (200 mg, 0.73 mmol), 5-fluoro-2-methylaniline (138 mg, 1.1 mmol), tris(dibenzylideneacetone)dipalladium (0) (34 mg, 0.037 μmol), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (35 mg, 0.073 mmol), and sodium tert-butoxide (211 mg, 2.2 mmol) in toluene (2 mL) was heated at 100° C. in an oil bath for 18 h. The mixture was cooled to room temperature, diluted with MeOH and filtered through a pad of Celite. The filtrate was concentrated over silica gel and purified using column chromatography (0-40% acetone in hexanes) to afford a tan solid that was about 90% pure. The material was dissolved in MeOH and loaded onto an Agilent AccuBOND II SCX solid phase extraction column. It was washed with MeOH followed by 2 M NH3 in MeOH. The title compound was obtained as a tan solid. MS (ESI, pos. ion) m/z: 362.1 (M+1).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated over silica gel
  4. custompurified
  5. customto afford a tan solid
  6. extractionloaded onto an Agilent AccuBOND II SCX solid phase extraction column
  7. washIt was washed with MeOH

출처 및 근거

ORD 기록
ord-299e22a496894bfda0b4ec1b02af75f7
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497269B2

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