Sulfuric Acid → HCID 59797078, compound

HRID 34019Notes

Reaction equation

HRID 34019 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[N:7][NH:8]2)=[CH:4][C:3]=1[C:20]#[N:21].S(=O)(=O)(O)[OH:23]>C(O)(=O)C.O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[N:7][NH:8]2)=[CH:4][C:3]=1[C:20]([NH2:21])=[O:23]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 59797063HCID 59797063, compound

Product 1

HCID 59797078HCID 59797078, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 89 mg of 6-fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1H-indazole-5-carbonitrile obtained by Example 100 in 0.4 mL of acetic acid and 0.4 mL of water was added 1.2 mL of concentrated sulfuric acid, and stirred at 110° C. for 50 minutes. After allowing to cool, ice was added, and extracted with a mixed solvent of 20 mL of ethyl acetate and 10 mL of tetrahydrofuran. The organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. After making the organic layer pass through an alumina pad (2.5 diameter ×2 cm), the solvent was evaporated, to afford 76 mg of the title compound as pale yellow crystals.

Workup

  1. temperatureto cool
  2. additionice was added
  3. extractionextracted with a mixed solvent of 20 mL of ethyl acetate and 10 mL of tetrahydrofuran
  4. washThe organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ec5d1b48389d430c827dd05007c46d52
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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