Sodium Iodide → HCID 137010778, compound

HRID 2206116Notes

Reaction equation

C[O:2][C:3]1[C:8]2[C:9]([C:21]3[CH:22]=[C:23]([C:26]([O:28][CH3:29])=[O:27])[S:24][CH:25]=3)=[N:10][N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:7]=2[CH:6]=[CH:5][N:4]=1.[I-].[Na+].Cl[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][N:11]2[C:7]3[CH:6]=[CH:5][NH:4][C:3](=[O:2])[C:8]=3[C:9]([C:21]3[CH:22]=[C:23]([C:26]([O:28][CH3:29])=[O:27])[S:24][CH:25]=3)=[N:10]2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 4-(4-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylate (75.0 mg) in acetonitrile (5 mL) were added sodium iodide (68.6 mg) and chloro(trimethyl)silane (0.232 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 to ethyl acetate/methanol) to give the title compound (49.7 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 to ethyl acetate/methanol)

Sources & evidence

ORD record: ord-2876d59bfb2845b6b47a3a7c6284bc98
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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