Dichloromethane → HCID 178432920, compound

HRID 245659Notes

Reaction equation

HRID 245659 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:8]([C@H:11]3[CH2:16][CH2:15][C@H:14]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[O:24])[CH2:19][CH2:18]4)[CH2:13][CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[C:33](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.ClCCl>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:33][C:2]1[C:3]2[N:4]([C:8]([C@H:11]3[CH2:12][CH2:13][C@H:14]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)=[O:24])[CH2:19][CH2:18]4)[CH2:15][CH2:16]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 178525158HCID 178525158, compound

Product 1

HCID 178432920HCID 178432920, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To benzyl trans-4-(4-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)piperazine-1-carboxylate (0.66 mmol, 300 mg) and potassium carbonate (0.991 mmol, 137 mg) in dioxane (2 ml). was added trimethylboroxine (1.982 mmol, 0.559 ml, 50 wt % solution in tetrahydrofuran) and nitrogen was bubbled through the suspension for a couple of minutes. Then 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride, complex with dichloromethane (0.066 mmol, 53.4 mg) was added and the reaction was stirred at 100° C. After two hours the reaction was cooled, filtered through decalite and rinsed with ethyl acetate and the filtrate concentrated under reduced pressure. The residue was purified using column chromatography (silica gel; dichloromethane/methanol 9/1) to give 224 mg of benzyl trans-4-(4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)piperazine-1-carboxylate.

Workup

  1. customwas bubbled through the suspension for a couple of minutes
  2. temperatureAfter two hours the reaction was cooled
  3. filtrationfiltered through decalite
  4. washrinsed with ethyl acetate
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-b2f91b347c124c91bdfb27a00651dad2
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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