2,3,5,6-Tetrafluorophenylhydrazine → 4-iodo-1-(2,3,5,6-tetrafluorophenyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1186808Notes

Reaction equation

F[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]=O.[F:11][C:12]1[C:17]([F:18])=[CH:16][C:15]([F:19])=[C:14]([F:20])[C:13]=1[NH:21][NH2:22]>CN1C(=O)CCC1>[I:10][C:6]1[CH:7]=[CH:8][N:9]=[C:2]2[N:21]([C:13]3[C:14]([F:20])=[C:15]([F:19])[CH:16]=[C:17]([F:18])[C:12]=3[F:11])[N:22]=[CH:4][C:3]=12

Participants

Conditions

Temperature: 184 °C

Procedure

To a 15 mL pressure bottle was added 2-fluoro-4-iodonicotinaldehyde (710 mg, 2.83 mmol), (2,3,5,6-tetrafluorophenyl)hydrazine (509 mg, 2.83 mmol), and anhydrous NMP (4 mL). The reaction mixture was flushed with argon, securely capped, and heated at 184° C. for 2.75 h. The reaction mixture was partitioned with ethyl acetate (300 mL), water (125 mL), and brine (50 mL). The organic layer was washed with water (4×40 mL) and brine (75 mL) and the combined aqueous layers were extracted with additional ethyl acetate (300 mL). The second organic layer was washed with water (4×60 mL), and brine (100 mL), and the combined organic layers were dried over sodium sulfate, and evaporated in vacuo to give 1.16 g (quantitative yield) of the title compound as a tan solid. LC/MS (Condition B): ret. T=3.92 min, (M+H)+ 393.89.

Workup

customThe reaction mixture was flushed with argon
customsecurely capped
customThe reaction mixture was partitioned with ethyl acetate (300 mL), water (125 mL), and brine (50 mL)
washThe organic layer was washed with water (4×40 mL) and brine (75 mL)
extractionthe combined aqueous layers were extracted with additional ethyl acetate (300 mL)
washThe second organic layer was washed with water (4×60 mL), and brine (100 mL)
dry with materialthe combined organic layers were dried over sodium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-7f390854fa874cb584c6795bad2b217f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673922B2

Reaction notes

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