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Potassium Carbonate → Benzenamine,4-[(6-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluoro-

HRID 2192147
Notes
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Reaction equation

HRID 2192147 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([N+]([O-])=O)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl.[NH2:29][C:30]1[CH:35]=[C:34]([F:36])[C:33]([OH:37])=[C:32]([F:38])[CH:31]=1>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([O:37][C:33]2[C:34]([F:36])=[CH:35][C:30]([NH2:29])=[CH:31][C:32]=2[F:38])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 179793386-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridineHCID 229263204-Amino-2,6-difluorophenol hydrochloride

Product 1

HCID 17979280Benzenamine,4-[(6-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluoro-

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

664 mg (3.36 mmol) of 6-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridine, 1.39 g (10.1 mmol) of powdered potassium carbonate and 877 mg (5.04 mmol) of sodium dithionite are suspended in 10 ml of DMSO. The mixture is degassed, and 915 mg (5.04 mmol) of 4-amino-2,6-difluorophenol hydrochloride are added. The mixture is heated at 120° C. for 4 hours. After addition of ethyl acetate, the mixture is filtered off with suction through celite, and the celite is washed with ethyl acetate. The filtrate is shaken three times with saturated sodium bicarbonate solution and with saturated, sodium chloride solution. The filtrate is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by column chromatography (silica gel 60, mobile phase: dichloromethane/methanol=50:1).

Workup

  1. customThe mixture is degassed
  2. filtrationthe mixture is filtered off with suction through celite
  3. washthe celite is washed with ethyl acetate
  4. dry with materialThe filtrate is dried over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by column chromatography (silica gel 60, mobile phase: dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-948cb4dc263042fbab3cddff008d2b7a
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329716B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes