Potassium Carbonate → 2-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-4-methylthiazole

HRID 79470Notes

Reaction equation

HRID 79470 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+].Cl.Cl[CH2:22][C:23]1[S:24][CH:25]=[C:26]([CH3:28])[N:27]=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]([CH2:22][C:23]2[S:24][CH:25]=[C:26]([CH3:28])[N:27]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 242788792-(Chloromethyl)-4-methyl-1,3-thiazole hydrochlorideHCID 178526562HCID 178526562, compound

Product 1

HCID 672597432-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-4-methylthiazoleYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-4-nitro-1H-indazole (0.500 g, 1.73 mmol) in DMF (8 mL) was added potassium carbonate (0.478 g, 3.46 mmol) at ambient temperature. After 15 minutes, 2-(chloromethyl)-4-methylthiazole hydrochloride was added. The mixture was allowed to stir at ambient temperature for 18 hours, concentrated under reduced pressure and diluted with DCM and brine. The organic phase was dried (phase separator silicone treated filter paper), and purified by silica gel chromatography (10-50% ether in DCM) to provide 2-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-4-methylthiazole (0.414 g, 60% yield) as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with DCM and brine
  3. customThe organic phase was dried
  4. addition(phase separator silicone treated filter paper)
  5. custompurified by silica gel chromatography (10-50% ether in DCM)

Sources & evidence

ORD record
ord-73db7473352d44a384cd196943dd28cd
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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