Potassium Carbonate → HCID 67261198, compound

HRID 79476Notes

Reaction equation

HRID 79476 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[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=1>CN(C=O)C>[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([I:1])=[N:3]2)=[N:24][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574316752-(Chloromethyl)-5-fluoropyridine hydrochlorideHCID 178526562HCID 178526562, compound

Product 1

HCID 67261198HCID 67261198, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-4-nitro-1H-indazole (1.0 g, 3.46 mmol) in DMF (20 mL) was added potassium carbonate (0.956 g, 6.92 mmol) and 2-(chloromethyl)-5-fluoropyridine hydrochloride (0.630 g, 3.46 mmol). The mixture was stirred at ambient temperature for 18 hours under nitrogen. The mixture was concentrated under vacuum and then diluted water (300 mL). The precipitated solids were collected by filtration and washed with water. The material was dried under high vacuum for 16 hours to give 1-((5-fluoropyridin-2-yl)methyl)-3-iodo-4-nitro-1H-indazole (0.968 g).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. filtrationThe precipitated solids were collected by filtration
  3. washwashed with water
  4. customThe material was dried under high vacuum for 16 hours

Sources & evidence

ORD record
ord-07ebd8f8742949afbc537b9816a0ab82
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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