2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 11710689, compound

HRID 2373214Notes

Reaction equation

[C:1]([O:5][C:6](=[O:19])[C:7]([CH2:16]OC)=[CH:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:20][C:21]1[N:25]([CH2:26][CH3:27])[N:24]=[CH:23][CH:22]=1.ClC1[C:30](=[O:41])C(C#N)=C(C#N)C(=O)C=1Cl.[C:42]([O-])(O)=O.[Na+]>C(O)(C)(C)C.C1COCC1>[CH2:26]([N:25]1[C:21]2=[N:20][C:16]([CH2:42][O:41][CH3:30])=[C:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:19])[C:8]([C:9]3[CH:10]=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=3)=[C:22]2[CH:23]=[N:24]1)[CH3:27]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of tert-butyl -2-(methoxymethyl)-3-(5-methyl-3-pyridyl)acrylate (1.26 g) and 5-amino-1-ethylpyrazole (481 mg) in tert-BuOH (14 ml) was heated at 90° C. for 3 hours. After cooling the mixture was dissolved in THF (14 ml). To this was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (982 mg) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:1) to give tert-butyl 1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (1.23 g) as a colorless crystal.

Workup

temperatureAfter cooling the mixture
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:1)

Sources & evidence

ORD record: ord-387b61e85c874762ac618a2ae2c55ca7
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459451B2

Reaction notes

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