Potassium Carbonate → HCID 178432918, compound

HRID 245741Notes

Reaction equation

HRID 245741 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:22]3[CH:23]=[CH:24][N:25]=[C:26](Cl)[C:21]3=[CH:20][N:19]=2)[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:22]3[CH:23]=[CH:24][N:25]=[C:26]([CH3:29])[C:21]3=[CH:20][N:19]=2)[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 178523379HCID 178523379, compound

Product 1

HCID 178432918HCID 178432918, compoundYield 56.4%

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 a suspension of benzyl((trans)-4-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methylcarbamate (6.58 g, 16.50 mmol) and potassium carbonate (3.42 g, 24.74 mmol) in 1,4-dioxan (200 ml) was added (after flushing with nitrogen) trimethylboroxine (13.84 ml, 49.5 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (1.217 g, 1.650 mmol). The reaction was stirred at 100° C. overnight. The reaction mixture was cooled to room temperature, filtered over Celite and Celite washed with ethyl acetate. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, ethyl acetate with gradient of 0 to 10% of methanol) to yield benzyl((trans)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methylcarbamate (3.52 g)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered over Celite and Celite
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography (silica gel, ethyl acetate with gradient of 0 to 10% of methanol)

Sources & evidence

ORD record
ord-6bd0e56f945b4df5841aff3abcc6146b
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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