Potassium tert-butoxide → 1H-Indazole

HRID 1810222Notes

Reaction equation

HRID 1810222 reaction equation
C([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][N:9]=1)C1C=CC=CC=1.CC(C)([O-])C.[K+]>CS(C)=O>[NH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[N:9]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178420212HCID 178420212, compound

Product 1

HCID 92211H-Indazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Benzyl-indazole is dissolved in dimethylsulfoxide and potassium tert-butoxide (1 M solution in tetrahydrofuran) is added at room temperature. Oxygen is then bubbled into the solution for 5 minutes. The reaction is allowed to stir at room temperature for 18 h. The reaction is quenched with aqueous saturated ammonium chloride then extracted three times with ethyl acetate. The combined organic extracts are dried over sodium sulfate, and concentrated. Purification by flash chromatography provides the deprotected indazole.

Workup

  1. customOxygen is then bubbled into the solution for 5 minutes
  2. customThe reaction is quenched with aqueous saturated ammonium chloride
  3. extractionthen extracted three times with ethyl acetate
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-62940f52d4534d01b8b76a743c6b1997
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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