Potassium Carbonate → HCID 67976141, compound

HRID 706653Notes

Reaction equation

HRID 706653 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+].Cl.Cl[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][CH3:31])[N:24]=1>CN(C=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]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][CH3:31])[N:24]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67975026HCID 67975026, compoundHCID 178526560HCID 178526560, compound

Product 1

HCID 67976141HCID 67976141, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-4-nitro-1H-indazole (1.5 g, 6.20 mmol) in DMF (0.5M, 12 mL) was added potassium carbonate (1.71 g, 12.4 mmol) at ambient temperature. After 15 minutes, 2-(chloromethyl)-6-ethoxypyridine hydrochloride (1.29 g, 6.20 mmol) was added. The mixture was allowed to stir at ambient temperature for 18 hours. The mixture was concentrated and diluted with ice-water (300 mL). Precipitated solids were collected by filtration, washed with water and dried under high vacuum overnight to provide 3-bromo-1-((6-ethoxypyridin-2-yl)methyl)-4-nitro-1H-indazole (1.21 g, 52% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ice-water (300 mL)
  3. customPrecipitated solids
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-664164314b194bea8391d9c234f0ffd5
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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