Water → 2-benzyl-5-nitroindazole

HRID 1815911Notes

Reaction equation

HRID 1815911 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[CH:7]=[C:6]2[C:10]([CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5]2)=[N: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 46531022-benzyl-5-nitroindazoleHCID 219520821-Benzyl-5-nitro-1H-indazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10 g (61.3 mmol) of 5-nitroindazole 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 water. The resulting slurry was filtered, rinsed once with water and dried in vacuo giving a beige solid. A 2.5 g portion of this crude material was purified by chromatography (SiO2, elution with 1:2 EtOAc-hexanes) giving 1-benzyl-5-nitro-1H-indazole and 2-benzyl-5-nitro-2H-indazole.

Workup

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

Sources & evidence

ORD record
ord-a5975e88735f420b98b6cbdd643f9ddf
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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