Ammonia → HCID 86725171, compound

HRID 2273315Notes

Reaction equation

[CH2:1]([S:3][C:4]1[C:5]([C:10]2[N:19]([CH3:20])[C:13]3=[N:14][CH:15]=[C:16](I)[CH:17]=[C:12]3[N:11]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].[F:21][C:22]([F:30])([F:29])[C:23]([F:28])([F:27])C([O-])=O.[Na+].N.C(=O)([O-])O.[Na+]>[Cu](I)I.C1(C)C(C)=CC=CC=1.CN1C(=O)CCC1>[CH2:1]([S:3][C:4]1[C:5]([C:10]2[N:19]([CH3:20])[C:13]3=[N:14][CH:15]=[C:16]([C:23]([F:28])([F:27])[C:22]([F:30])([F:29])[F:21])[CH:17]=[C:12]3[N:11]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-(3-ethylsulfanyl-pyridin-2-yl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine (835 mg), sodium pentafluoropropionate (2.0 g), copper iodide (2.0 g), NMP (10 ml) and xylene (50 ml) was stirred while heating to 150° C. for 8 hours. After allowing to cool to room temperature, to the reaction mixture were added 40% aqueous ammonia solution and saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-(3-ethylsulfanyl-pyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine (303 mg), which is hereinafter referred to as “the present compound 6”.

Workup

temperatureto cool to room temperature, to the reaction mixture
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-eedda23a66674ecaa4be84b6b4389ca9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120823B2

Reaction notes

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