Ethyl Acetate → Benzenamine,4-[(6-chloro-3-methyl-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoro-

HRID 2192161Notes

Reaction equation

COC([N:5]1[C:9]2=[N:10][C:11]([Cl:15])=[CH:12][C:13](Cl)=[C:8]2[C:7]([CH3:16])=[CH:6]1)=O.C(=O)([O-])[O-].[K+].[K+].[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([F:31])[CH:25]=1.C(OCC)(=O)C>CS(C)=O>[Cl:15][C:11]1[N:10]=[C:9]2[NH:5][CH:6]=[C:7]([CH3:16])[C:8]2=[C:13]([O:30][C:27]2[CH:28]=[CH:29][C:24]([NH2:23])=[CH:25][C:26]=2[F:31])[CH:12]=1

Participants

Conditions

Temperature: 120 °C

Procedure

300 mg (1.16 mmol) of methyl-4,6-dichloro-3-methyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate and 320 mg (2.32 mmol) of powdered potassium carbonate are suspended in 9 ml of DMSO. The mixture is degassed, and 442 mg (3.48 mmol) of 4-amino-2-fluorophenol 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-1f8f2ae2bbd6410b9841019a686c8869
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

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