Bromocyclopentane → HCID 68295537, compound

HRID 1501704Notes

Reaction equation

HRID 1501704 reaction equation
[C:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=[C:8]([C:17]([O:19][CH3:20])=[O:18])[C:7]=2[CH:6]=[N:5]1)(=O)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:28]1[CH2:32]CC[CH2:29]1>C(#N)C>[CH:1]1([N:4]2[C:12]3[CH:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=[C:8]([C:17]([O:19][CH3:20])=[O:18])[C:7]=3[CH:6]=[N:5]2)[CH2:32][CH2:28][CH2:29][CH2:2]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 10796Cesium carbonateHCID 68295765HCID 68295765, compound

Product 1

HCID 68295537HCID 68295537, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methyl 1-acetyl-6-(trifluoromethyl)-1H-indazole-4-carboxylate (1 equiv.) in acetonitrile (3 mL per 1 mmol), cesium carbonate (1.5 equiv.) was added followed by bromocyclopentane (2 equiv.). The reaction mixture was stirred at 90° C. for 3-4 h. On completion of reaction, acetonitrile was removed under reduced pressure and water was added. Extraction was carried out using ethyl acetate and the combined organic layers washed with water, brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography to obtain methyl 1-cyclopentyl-6-(trifluoromethyl)-1H-indazole-4-carboxylate (yield 30-35%). The structure was confirmed as the desired regioisomer by NOE.

Workup

  1. customwas removed under reduced pressure and water
  2. additionwas added
  3. extractionExtraction
  4. washthe combined organic layers washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customSolvent was removed under reduced pressure and residue
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0e09c3175c4743dbb14429aa2deec687
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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