Sodium Iodide → 3-phenyl-1-(3-thienyl)-1,6-dihydro-7H-pyrazolo[3,4-c]pyridin-7-one

HRID 2205987Notes

Reaction equation

C[O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][N:9]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[C:8]=12.[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[C:12]1([C:11]2[C:7]3[CH:6]=[CH:5][NH:4][C:3](=[O:2])[C:8]=3[N:9]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[N:10]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 7-methoxy-3-phenyl-1-(3-thienyl)-1H-pyrazolo[3,4-c]pyridine (28.5 mg) in acetonitrile (10 mL) were added sodium iodide (27.8 mg) and chloro(trimethyl)silane (81 mg), and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane), and crystallized from ethyl acetate and hexane to give the title compound (24.5 mg).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
customcrystallized from ethyl acetate and hexane

Sources & evidence

ORD record: ord-ee76ea09ee114ef4b96c1f5078987142
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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