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2-Chloro-5-trifluoroacetylthiophene → 1-(5-Chlorothiophen-2-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol

HRID 244425
Notes
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Reaction equation

HRID 244425 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[N:6]=[CH:5]2.C([Li])CCC.[Cl:23][C:24]1[S:25][C:26]([C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])=[CH:27][CH:28]=1>C1COCC1.O>[Cl:23][C:24]1[S:25][C:26]([C:29]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:6]=[CH:5]3)([OH:34])[C:30]([F:31])([F:32])[F:33])=[CH:27][CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 27579322-Chloro-5-trifluoroacetylthiopheneHCID 468307945-bromo-1-(4-fluorophenyl)-1H-indazoleHCID 178418339Butyllithium

Product 1

HCID 249620151-(5-Chlorothiophen-2-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanolYield 15.5%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a chilled (−78° C.) stirred solution of 1.5 g (5.0 mmol) of 5-bromo-1-(4-fluorophenyl)-1H-indazole in THF was added 2.0 mL (5.0 mmol) of n-butyllithium dropwise followed by 1.0 g (4.6 mmol) of 2-chloro-5-trifluoroacetylthiophene in one portion. After 30 minutes, the mixture was diluted with 10 mL of water, warmed to room temperature and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate-hexanes (gradient 10-30%) to afford 300 mg (15.5%) of the title compound. MS m/z 427.82 (MH+).

Workup

  1. temperaturewarmed to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9004be7ed1c449df989909ccd852b7a8
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658637B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes