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3-Fluoroaniline → HCID 59409476, 화합물

HRID 659954
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HRID 659954 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:16]([CH2:17][CH2:18][F:19])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:5]=[CH:4][N:3]=1.[F:27][C:28]1[CH:29]=[C:30]([NH2:34])[CH:31]=[CH:32][CH:33]=1.C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CC(C)([O-])C.[Na+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:19][CH2:18][CH2:17][N:16]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:34][C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([F:27])[CH:29]=2)[CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 97423-FluoroanilineHCID 25517Ammonium ChlorideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 86643499HCID 86643499, 화합물

생성물 1

HCID 59409476HCID 59409476, 화합물수율 38.2%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
180 °C

실험 절차

In a 5 mL microwave vessel (Biotage) are weighted together 185 mg (0.5 mmole) of 2-(2-Chloro-pyridin-4-yl)-1-(2-fluoro-ethyl)-3-(4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine, 67 mg (0.6 mmoles) of 3-fluorophenyl amine, 2 mg of palladium acetate, 7 mg of biphenylyl dicyclohexylphosphine and 67 mg (0.7 mmole) of sodium t-butoxide in 2.5 mL of toluene. The reaction mixture is then heated at 180° C. for 10 min. under microwave conditions. The reaction mixture is poured into ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. After concentration the solid residue is purified by chromatography on silica gel (ethyl acetate/hexane 1/1) to give 85 mg of {4-[1-(2-Fluoro-ethyl)-3-(4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl]-pyridin-2-yl}-(3-fluoro-phenyl)-amine as white solid.

후처리

  1. customIn a 5 mL microwave vessel (Biotage) are weighted together
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentration the solid residue
  6. customis purified by chromatography on silica gel (ethyl acetate/hexane 1/1)

출처 및 근거

ORD 기록
ord-f3390600c1fc42f08045e461c41a568f
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084395B2

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