Water → HCID 67259890, compound

HRID 79255Notes

Reaction equation

HRID 79255 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:20]([N:4]1[C:5]2[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=2)[C:2]([I:1])=[N:3]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178526562HCID 178526562, compound

Product 1

HCID 67259890HCID 67259890, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

3-Iodo-4-nitro-1H-indazole (0.50 g; 1.73 mmol) was dissolved with stirring in dimethylformamide (15 mL) under an atmosphere of nitrogen. Potassium carbonate (0.478 g; 3.46 mmol) was added followed by benzyl bromide (0.325 g; 1.90 mmol). The mixture was stirred for 16 hours at 25° C. The mixture was added to water (50 mL) and ethyl acetate (50 mL) with stirring. The mixture was transferred to a reparatory funnel and the phases were separated. The ethyl acetate phase was dried over sodium sulfate, filtered and concentrated under vacuum. The crude product was purified by silica gel chromatography, eluting with hexane/ethyl acetate (5:1). The fractions containing product were concentrated under vacuum to give the 1-benzyl-3-iodo-4-nitro-1H-indazole as a yellow oil (456 mg).

Workup

  1. stirringwith stirring
  2. customThe mixture was transferred to a reparatory funnel
  3. customthe phases were separated
  4. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with hexane/ethyl acetate (5:1)
  9. additionThe fractions containing product
  10. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-543b47ddfb1240c2ac0b87c04449be9f
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…