Dimethylformamide → 1-benzyl-4-nitro-1H-indazole

HRID 706734Notes

Reaction equation

HRID 706734 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:6]([N:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[N:7]1)[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 180574-Nitroindazole

Product 1

HCID 213272561-benzyl-4-nitro-1H-indazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Nitro-1H-indazole (1.0 g, 6.13 mmol) and potassium carbonate (1.69 g, 12.3 mmol) were added to DMF and stirred at room temperature overnight. Water (50 mL) was added and the product was extracted with ethyl acetate and dried over magnesium sulfate. Crude, brown solid was purified on silica gel using hexanes/ethyl acetate. First isolated peak (730 mg) was the desired 1-benzyl regio-isomer, as confirmed by NMR.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. customCrude, brown solid was purified on silica gel

Sources & evidence

ORD record
ord-ded6653aca5c4fcf9e0eb193b99b5d5a
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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