Potassium Carbonate → 3-iodo-1-((6-methoxypyridin-2-yl)methyl)-4-nitro-1H-indazole

HRID 79295Notes

Reaction equation

HRID 79295 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[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[N:23]=1>CN(C=O)C>[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[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[N:23]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 100815502-(Bromomethyl)-6-methoxypyridineHCID 178526562HCID 178526562, compound

Product 1

HCID 672611043-iodo-1-((6-methoxypyridin-2-yl)methyl)-4-nitro-1H-indazoleYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-iodo-4-nitro-1H-indazole (5.01 g, 17.3 mmol) in DMF (40 mL) was added K2CO3 (4.79 g, 34.7 mmol) and 2-(bromomethyl)-6-methoxypyridine (4.20 g, 20.8 mmol). The reaction mixture was stirred for 4 hours. The reaction mixture was concentrated to remove DMF, diluted with EtOAc and washed with H2O and brine. The organic phase was dried (Na2SO4) and concentrated. Silica gel chromatography (EtOAc/Hexane 1:5) gave the desired product (5.68 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove DMF
  3. additiondiluted with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-08d8152450e443d195c0642c917cc2a7
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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