Potassium Carbonate → 4-[(6-Chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline

HRID 2192154Notes

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+].[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([F:36])[CH:30]=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:35][C:32]2[CH:33]=[CH:34][C:29]([NH2:28])=[CH:30][C:31]=2[F:36])[CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1.80 g (9.11 mmol) of 6-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridine, 3.78 g (27.3 mmol) of potassium carbonate and 3.17 g (18.2 mmol) of sodium dithionite in 26 ml of DMSO is degassed. 2.32 g (18.2 mmol) of 4-amino-2-fluorophenol are added, and the mixture is heated at 120° C. for 4 hours. The mixture is then diluted with ethyl acetate and filtered off with suction through Celite®. The filtrate is washed twice with sodium carbonate and once with sodium chloride solution, dried over sodium sulfate and concentrated. The product is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 100:2).

Workup

customis degassed
filtrationfiltered off with suction through Celite®
washThe filtrate is washed twice with sodium carbonate and once with sodium chloride solution
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe product is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 100:2)

Sources & evidence

ORD record: ord-4372d3948fd946a99090e4c0b0f13f33
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

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