Potassium Carbonate → 3-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one

HRID 79427Notes

Reaction equation

HRID 79427 reaction equation
[Br: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+].Br[CH2:21][C:22]1[C:23](=[O:29])[N:24]([CH3:28])[CH:25]=[CH:26][CH:27]=1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:21][C:22]2[C:23](=[O:29])[N:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12272663HCID 12272663, compoundHCID 178526560HCID 178526560, compound

Product 1

HCID 672613133-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-oneYield 74.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-4-nitro-1H-indazole (Preparation B; 0.49 g, 2.04 mmol) was dissolved in dimethyl formamide (5 mL). Potassium carbonate (1.13 g, 8.15 mmol) was added followed by 3-(bromomethyl)-1-methylpyridin-2(1H)-one (0.41 g, 2.04 mmol). The mixture was stirred at ambient temperature for two days. The mixture was diluted with ethyl acetate (8 mL) and concentrated under vacuum to give a dark solid which was dried overnight under high vacuum. This material was dissolved in ethyl acetate (80 mL) and washed with water (40 mL). The aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under vacuum to give a green solid. This material was triturated with diethyl ether and the solids were collected by filtration and dried under high vacuum to give 3-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one as a beige solid (552 mg).

Workup

  1. concentrationconcentrated under vacuum
  2. customto give a dark solid which
  3. customwas dried overnight under high vacuum
  4. dissolutionThis material was dissolved in ethyl acetate (80 mL)
  5. washwashed with water (40 mL)
  6. extractionThe aqueous layer was extracted twice with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customto give a green solid
  10. customThis material was triturated with diethyl ether
  11. filtrationthe solids were collected by filtration
  12. customdried under high vacuum

Sources & evidence

ORD record
ord-7ded0357e0ec4a5d8d67632d0fa32272
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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