Carbon Dioxide → HCID 22260957, compound

HRID 1610116Notes

Reaction equation

HRID 1610116 reaction equation
Br[C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1.C([Li])CCC.[C:25](=[O:27])=[O:26].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[F:17][C:13]1[CH:12]=[C:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([C:25]([OH:27])=[O:26])[C:3]=3[O:18][CH3:19])[NH:7][N:6]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 22261064HCID 22261064, compoundHCID 178418339Butyllithium

Product 1

HCID 22260957HCID 22260957, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A total of 230 mg of 5-bromo-3-(3-fluoro-phenyl)-4-methoxy-1H-indazole obtained in Production Example II-2-c was dissolved in 4.78 ml of tetrahydrofuran, and 0.99 ml of a 1.59 M solution of n-butyllithium in hexane was added under stirring at −78° C. After stirring at −78° C. for 30 minutes, dry ice was added. After stirring at the same temperature for 10 minutes, saturated aqueous ammonium chloride solution was added. The mixture was extracted with ethyl acetate, and the resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:1), to give 41.1 mg of the title compound.

Workup

  1. stirringAfter stirring at −78° C. for 30 minutes
  2. stirringAfter stirring at the same temperature for 10 minutes
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe resulting organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-357969daa86e4fdbb7a9a4a7cc65560f
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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