Water → HCID 22260662, compound

HRID 503131Notes

Reaction equation

HRID 503131 reaction equation
Br[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[N:7]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:6]=1)=O.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.C(=O)([O-])O.[Na+].O>O1CCCC1CO>[N:24]1[C:3]([C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=3)[N:7]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:6]=2)=[CH:2][N:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=12

Participants

6

Reactant 4

HCID 962WaterHCID 104392-AminopyridineHCID 516892Sodium BicarbonateHCID 22260795HCID 22260795, compound

Product 1

HCID 22260662HCID 22260662, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

A total of 0.88 g of tert-butyl 3-(2-bromoacetyl)-5-nitro-1H-1-indazolecarboxylate was dissolved in 10 ml of tetrahydrofuran-methanol (1:1), and 240 mg of 2-aminopyridine and 210 mg of sodium hydrogencarbonate were added, followed by heating under reflux for 1 hour. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The mixture was washed with water, dried over magnesium sulfate and the solvent was removed. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:7), to give 0.38 g of the title compound as a pale yellow powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe mixture was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:7)

Sources & evidence

ORD record
ord-13bf38d31cb1416c820964269be6ee76
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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