Water → HCID 22933575, compound

HRID 1269839Notes

Reaction equation

HRID 1269839 reaction equation
[OH-].[Li+].[CH3:3][S:4]([O:7][C:8]1[C:9]([O:20][CH3:21])=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13](C(=O)C)[N:12]=[CH:11]2)(=[O:6])=[O:5].O>O1CCCC1.CO>[CH3:3][S:4]([O:7][C:8]1[C:9]([O:20][CH3:21])=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[CH:11]2)(=[O:5])=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86593611HCID 86593611, compound

Product 1

HCID 22933575HCID 22933575, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 2M-aqueous lithium hydroxide solution (0.352 ml, 0.704 mmol) was added to a solution of 1-acetyl-4-methoxy-1H-indazol-5-yl methanesulfonate (100 mg, 0.352 mmol) in a mixture of tetrahydrofuran (1.0 ml) and methanol (1.0 ml) at room temperature. After 1 hour, the resulting mixture was poured into water (10 ml) and extracted with ethyl acetate (20 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 4-methoxy-1H-indazol-5-yl methanesulfonate (80 mg, 94%).

Workup

  1. extractionextracted with ethyl acetate (20 ml×2)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe organic layer dried
  4. concentrationwas concentrated under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9aceaa6338e14e18b9a80f583ccac2bb
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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