3-Fluoroaniline → HCID 59409476, compound

HRID 659954Notes

Reaction equation

HRID 659954 reaction equation
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

Participants

8

Reactant 5

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

Product 1

HCID 59409476HCID 59409476, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
180 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f3390600c1fc42f08045e461c41a568f
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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