Allyl bromide → HCID 131721158, compound

HRID 1418294Notes

Reaction equation

HRID 1418294 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+].[CH2:27](Br)[CH:28]=[CH2:29].[Cl-].[NH4+]>C(OCC)C.C(#N)C>[CH2:29]([O:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:20])=[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])[CH:6]=1)[CH:28]=[CH2:27]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 15390589HCID 15390589, compound

Product 1

HCID 131721158HCID 131721158, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

An acetonitrile (10 mL) solution of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.69 g, 2.33 mmol), potassium carbonate (0.24 g, 1.74 mmol) and allylbromide (0.22 mL, 2.56 mmol) was stirred for 4.5 hours under reflux. A saturated ammonium chloride solution (10 mL) and diethyl ether (10 mL) were added to the resulting mixture, and the organic layer was separated and then the aqueous layer was extracted with diethyl ether (10 mL×2 times). The organic layer combined was washed with a saturated sodium chloride solution (15 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=1/2) to obtain a white solid of 2-(5-allyloxy-4-chloro-2-fluorophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.47 g, yield:62.9%).

Workup

  1. temperatureunder reflux
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with diethyl ether (10 mL×2 times)
  4. washThe organic layer combined was washed with a saturated sodium chloride solution (15 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=1/2)

Sources & evidence

ORD record
ord-9e8f9f987aaa401eb534cfb19853456e
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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