Potassium Carbonate → HCID 67976294, compound

HRID 706698Notes

Reaction equation

HRID 706698 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+].Br[CH2:21][C:22]1[C:23](=[O:29])[N:24]([CH3:28])[CH:25]=[CH:26][CH:27]=1>CN(C=O)C.C(Cl)Cl>[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])[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 122726633-(bromomethyl)-1-methylpyridin-2(1H)-oneHCID 178526562HCID 178526562, compound

Product 1

HCID 67976294HCID 67976294, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3-Iodo-4-nitro-1H-indazole (0.38 g, 1.3 mmol) was reacted with K2CO3 (0.36 g, 2.6 mmol) in DMF (4 mL) for 15 minutes. 3-(Bromomethyl)-1-methylpyridin-2(1H)-one (0.28 g, 1.4 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was diluted with CH2Cl2 (30 mL), filtered and concentrated. The residue was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated. The residue was suspended in EtOAc (8 mL), stirred for 20 minutes and then filtered to provide 3-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one (0.27 g, 50% yield) as a solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was partitioned between CHCl3 and saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. stirringstirred for 20 minutes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b5e08d37c2c94522b7536fad5c6c969d
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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