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

HRID 2192147Notes

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

Participants

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

customThe mixture is degassed
filtrationthe mixture is filtered off with suction through celite
washthe celite is washed with ethyl acetate
dry with materialThe filtrate is dried over sodium sulfate
customthe solvent is removed under reduced pressure
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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