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

HRID 16418
Notes
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Reaction equation

HRID 16418 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 (from example XXX), 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 (from example XXXII) 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 (diatomaceous earth) and the filtercake is washed with ethyl acetate. The filtrate is extracted three times with sat. sodium bicarbonate solution and with sat. 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 (silical gel 60, mobile phase: DCM:methanol=50:1).

Workup

  1. customThe mixture is degassed
  2. filtrationthe mixture is filtered off with suction through CELITE (diatomaceous earth)
  3. washthe filtercake is washed with ethyl acetate
  4. extractionThe filtrate is extracted three times with sat. sodium bicarbonate solution
  5. dry with materialThe filtrate is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by column chromatography (silical gel 60, mobile phase: DCM:methanol=50:1)

Sources & evidence

ORD record
ord-e9fbf9faaf5145ada6139bffefef77be
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737153B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes