Water → (3-Amino-2-fluoro-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 60092Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[C:14]=3[F:22])=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.O>O1CCCC1.C(OCC)(=O)C>[NH2:19][C:15]1[C:14]([F:22])=[C:13]([C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[NH:8][CH:9]=2)=[O:12])[CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-fluoro-3-nitro-phenyl)-methanone (18, 2.27 g, 6.23 mmol) in 200 mL of tetrahydrofuran and 200 mL of ethyl acetate, stannous chloride, dehydrate (4.85 g, 2.15 mmol) is added. The reaction is heated at 60° C. for 3 days, then 300 mL of water and 200 mL of ethyl acetate are added. The mixture is treated with celite and filtered. Brine is added, the organic layer is separated, dried over magnesium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (19, 972 mg).

Workup

additionThe mixture is treated with celite and
filtrationfiltered
additionBrine is added
customthe organic layer is separated
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationthe filtrate is concentrated under vacuum
customThe resulting material is purified by silica gel column chromatography
washeluting with ethyl acetate and hexane
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-e58f7501039241dbbcddf1e084e1de49
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440969B2

Reaction notes

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