Bromocyclopentane → HCID 131721161, compound

HRID 1418297Notes

Reaction equation

HRID 1418297 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:17](=[O:18])[C:12]3=[CH:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:27]1(Br)[CH2:31][CH2:30][CH2:29][CH2:28]1.[Cl-].[NH4+]>C(OCC)C.C(#N)C>[Cl:1][C:2]1[C:7]([O:8][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:6][C:5]([N:9]2[C:17](=[O:18])[C:12]3=[CH:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1

Participants

7

Reactant 4

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 15390589HCID 15390589, compound

Product 1

HCID 131721161HCID 131721161, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

An acetonitrile (20 mL) solution of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.46 g, 1.54 mmol), potassium carbonate (0.16 g, 1.16 mmol) and cyclopentylbromide (0.18 mL, 1.69 mmol) was stirred for 2 hours under reflux. A saturated ammonium chloride solution (20 mL) and diethyl ether (20 mL) were added to the resulting mixture, and the organic layer was separated and then the aqueous layer was extracted with diethyl ether (20 mL×2 times). The organic layer combined was washed with a saturated sodium chloride solution (25 mL) and dried over anhydrous magnesium sulfate. After removal of magnesium sulfate by filtration, the filtrate was evaporated to give crude product, which was purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/1) to obtain a pale yellow oil of 2-(4-chloro-5-cyclopentyloxy-2-fluorophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.49 g, yield:87.5%).

Workup

  1. temperatureunder reflux
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with diethyl ether (20 mL×2 times)
  4. washThe organic layer combined was washed with a saturated sodium chloride solution (25 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of magnesium sulfate
  7. filtrationby filtration
  8. customthe filtrate was evaporated
  9. customto give crude product, which
  10. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-84206ff77cd9491a8d4b99d9a6fb26c4
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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