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Water → 6-Fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1-trityl-1H-indazole-5-carboxylic Acid

HRID 34017
Notes
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Reaction equation

HRID 34017 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]([OH:22])=[O:21].[H-].[Na+].[C:25](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C)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][N:8]2[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:4][C:3]=1[C:20]([OH:22])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 59797186HCID 59797186, compound

Product 1

HCID 689303146-Fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1-trityl-1H-indazole-5-carboxylic AcidYield 58.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Under ice cooling, to a solution of 350 mg of 6-fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1H-indazole-5-carboxylic acid obtained by Example 101 in 6 mL of N,N-dimethylformamide was added 103 mg of 60% sodium hydride, stirred for 30 minutes, then added with 390 mg of trityl chloride, and stirred at this temperature for 20 minutes and at room temperature for 1 hour. The reaction solution was added with water and extracted with 80 mL of ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (ethylacetate:toluene=1:9), to afford 370 mg of the title compound as bright yellow crystals.

Workup

  1. stirringstirred at this temperature for 20 minutes and at room temperature for 1 hour
  2. extractionextracted with 80 mL of ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe crude product was purified
  7. customseparated by silica gel column chromatography (ethylacetate:toluene=1:9)

Sources & evidence

ORD record
ord-d65698d886434ecb9ac6328f52823d70
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes