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

HRID 16421

Reaction equation

C([N:4]1[C:8]2=[N:9][C:10]([Cl:14])=[CH:11][C:12](Cl)=[C:7]2[C:6]([CH3:15])=[CH:5]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([F:30])[CH:24]=1.C(OCC)(=O)C>CS(C)=O>[Cl:14][C:10]1[N:9]=[C:8]2[NH:4][CH:5]=[C:6]([CH3:15])[C:7]2=[C:12]([O:29][C:26]2[CH:27]=[CH:28][C:23]([NH2:22])=[CH:24][C:25]=2[F:30])[CH:11]=1

Participants

Conditions

Temperature: 120 °C

Procedure

300 mg (1.16 mmol) of 1-acetyl-4,6-dichloro-3-methyl-1H-pyrrolo[2,3-b]pyridine (from example XL) 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 (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 (silica gel 60, mobile phase: DCM:methanol=50:1).

Workup

customThe mixture is degassed
filtrationthe mixture is filtered off with suction through CELITE (diatomaceous earth)
washthe filtercake is washed with ethyl acetate
extractionThe filtrate is extracted three times with sat. sodium bicarbonate solution
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: DCM:methanol=50:1)

Sources & evidence

ORD record: ord-f54b7a1f971e4a7496946caf6e8bee25
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737153B2

Linked notes

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