Dichloromethane → HCID 67364106, compound

HRID 245654Notes

Reaction equation

HRID 245654 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:8]([CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[C:17](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.ClCCl>O1CCOCC1>[CH3:17][C:2]1[C:3]2[N:4]([C:8]([CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 71743145HCID 71743145, compound

Product 1

HCID 67364106HCID 67364106, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Through a suspension of 8-chloro-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazine (2.23 mmol, 531 mg) and potassium carbonate (3.35 mmol, 463 mg) in dioxane (1.5 mL) was bubbled nitrogen for 5 minutes and then trimethylboroxine (4.47 mmol, 1.249 mL, 50 wt % solution in tetrahydrofuran) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (0.223 mmol, 181 mg) were added. After heating the reaction at 100° C. for one hour the reaction mixture was filtered and concentrated in vacuo. Dichloromethane and water were added, the organic layer separated, dried (sodium sulfate) and concentrated in vacuo to yield 374 mg 8-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazine.

Workup

  1. customwas bubbled nitrogen for 5 minutes
  2. temperatureAfter heating
  3. customthe reaction at 100° C. for one hour the reaction mixture
  4. filtrationwas filtered
  5. concentrationconcentrated in vacuo
  6. additionDichloromethane and water were added
  7. customthe organic layer separated
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5027fac106e34b259b74f31b2102f64e
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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