Sodium Iodide → 4-(1-tert-butyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

HRID 2206137Notes

Reaction equation

[C:1]([N:5]1[C:13]2[CH:12]=[CH:11][N:10]=[C:9]([O:14]C)[C:8]=2[C:7]([C:16]2[CH:17]=[C:18]([C:21]([NH2:23])=[O:22])[S:19][CH:20]=2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[I-].[Na+].Cl[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[C:1]([N:5]1[C:13]2[CH:12]=[CH:11][NH:10][C:9](=[O:14])[C:8]=2[C:7]([C:16]2[CH:17]=[C:18]([C:21]([NH2:23])=[O:22])[S:19][CH:20]=2)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-(1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide (500 mg) in acetonitrile (30 mL) were added sodium iodide (567 mg) and chloro(trimethyl)silane (1.92 mL), and the mixture was stirred at 50° C. for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/methanol) to give the title compound (475 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/methanol)

Sources & evidence

ORD record: ord-69099596da944f12a6b9eb5786a9e151
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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