Aniline → HCID 178509226, compound

HRID 1943896Notes

Reaction equation

HRID 1943896 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+].BrC1C2[C:62](=[N:63]C=C([N+]([O-])=O)C=2)[N:61](COCC[Si](C)(C)C)[N:60]=1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH:61]1[C:62]2=[N:63][CH:4]=[CH:5][CH:6]=[C:7]2[C:2]([NH2:1])=[N:60]1

Participants

7

Reactant 4

HCID 6115AnilineHCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 670887183-bromo-5-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 178509226HCID 178509226, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Aniline (0.035 mL, 0.386 mmol), Pd2 dba3 (0.024 g, 0.0257 mmol), Xantphos (0.030 g, 0.0714 mmol), K3PO4 (0.120 g, 0.566 mmol) was added to a suspension of 3-bromo-5-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine (0.096 g, 0.257 mmol) in toluene (10 mL), and the mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature and filtered through celite. The filter cake was washed with ethyl acetate. The combined filtrate was concentrated to give the crude product 5-nitro-N-phenyl-1-(2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-3-amine. This material was used without purification in the next step.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered through celite
  4. washThe filter cake was washed with ethyl acetate
  5. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-420694fde1004961830f2f3ad11520d0
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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