Water → 1-Benzyl-5-nitro-1H-indazole

HRID 983424

Reaction equation

HRID 983424 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[C:19]1([CH2:25]Br)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:25]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[N:8]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:25]([N:8]1[CH2:7][C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 215015-Nitroindazole

Product 2

HCID 219520821-Benzyl-5-nitro-1H-indazoleHCID 22560083HCID 22560083, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-nitroindazole (10 g, 61.3 mmol) in DMF (100 mL) was added K2CO3 (12.7 g, 91.9 mmol) and PhCH2Br (7.29 mL, 61.3 mmol). The resulting mixture was stirred at RT for 3.5 days, then poured into 400 mL of H2O. The resulting slurry was filtered, rinsed once with water and dried in vacuo giving a beige solid. A portion of this crude material (2.5 g) was purified by chromatography (SiO2, elution with 1:2 EtOAc-hexanes) giving 1-benzyl-5-nitro-1H-indazole and 2-benzyl-5-nitro-1H-indazole.

Workup

  1. filtrationThe resulting slurry was filtered
  2. washrinsed once with water
  3. customdried in vacuo
  4. customgiving a beige solid
  5. customA portion of this crude material (2.5 g) was purified by chromatography (SiO2, elution with 1:2 EtOAc-hexanes)

Sources & evidence

ORD record
ord-a143097e57ae4084916693887d2a7f21
Source dataset
uspto-grants-2005_03
Patent number
US06864255B2

Linked notes

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