2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178468515, compound

HRID 336847Notes

Reaction equation

HRID 336847 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([C:9](=[CH:15][C:16]2[O:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)=[CH:5][CH:4]=1.[NH2:24][C:25]1[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C([O-])(O)=O.[Na+]>CCCCO.C1COCC1>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]2[N:24]=[C:25]3[NH:26][N:27]=[C:28]([CH3:30])[C:29]3=[C:15]([C:16]3[O:17][C:18]([CH3:21])=[CH:19][CH:20]=3)[C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 516892Sodium BicarbonateHCID 67074332HCID 67074332, compound

Product 1

HCID 178468515HCID 178468515, compoundYield 15.5%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.76 g (2.41 mmol) of ethyl 2-(4-methoxybenzoyl)-3-(5-methylfuran-2-yl)acrylate and of 0.23 g (2.41 mmol) of 3-amino-5-methyl-pyrazole is heated to 140° C. in 6 ml of n-BuOH for 24 h. The mixture is then cooled to room temperature and 0.55 g (2.4 mmol) of DDQ in 6 ml of THF is added. The mixture is stirred at room temperature for 1 h. The mixture is then poured onto a saturated solution of NaHCO3 then extracted with ethyl acetate. The organic phase is washed in a saturated solution of sodium chloride, dried over sodium sulfate, filtered, and concentrated. The mixture is then purified using reverse-phase HPLC to yield 146 mg (15%) of ethyl 6-(4-methoxyphenyl)-3-methyl-4-(5-methylfuran-2-yl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate in the form of a yellow solid.

Workup

  1. extractionthen extracted with ethyl acetate
  2. washThe organic phase is washed in a saturated solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe mixture is then purified

Sources & evidence

ORD record
ord-ee43a70bd2dc436dbdc95b1e329f2f6d
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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