Bromocyclopentane → HCID 67466686, compound

HRID 1501699Notes

Reaction equation

HRID 1501699 reaction equation
[C:1]([N:4]1[C:12]2[CH:11]=[C:10]([Cl:13])[CH:9]=[C:8]([C:14]([O:16][CH3:17])=[O:15])[C:7]=2[CH:6]=[N:5]1)(=O)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:25]1[CH2:29]CC[CH2:26]1>C(#N)C>[Cl:13][C:10]1[CH:9]=[C:8]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[CH:6]=[N:5][N:4]([CH:1]3[CH2:29][CH2:25][CH2:26][CH2:2]3)[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 10796Cesium carbonateHCID 86703442HCID 86703442, compound

Product 1

HCID 67466686HCID 67466686, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methyl 1-acetyl-6-chloro-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 were washed with water, brine and dried over anhydrous Na2SO4. The solvent was then removed under reduced pressure and residue was purified by silica gel column chromatography to obtain methyl 6-chloro-1-cyclopentyl-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 were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was then removed under reduced pressure and residue
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-663e67d58cb64cff98a49ea69dc5d801
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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