Dichloromethane → HCID 178476589, compound

HRID 245766Notes

Reaction equation

[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19](Cl)[C:14]3=[CH:13][N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[C:21](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.ClCCl>O1CCOCC1>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:21])[C:14]3=[CH:13][N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 95 °C

Procedure

To (cis)-4-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (48.0 mmol, 14.09 g) in dry dioxane (275 ml) under a nitrogen atmosphere were added dry potasium carbonate (71.9 mmol, 9.94 g), trimethylboroxine (144 mmol, 20.03 ml, 50 wt % solution in tetrahydrofuran) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (4.80 mmol, 3.88 g) and the reaction mixture was stirred at 95° C. for one hour. The reaction mixture was cooled to room temperature, filtered over decalite, the filter rinsed with dioxane and the filtrate concentrated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 6% of methanol) to give (cis)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (12.8 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered over decalite
washthe filter rinsed with dioxane
concentrationthe filtrate concentrated in vacuo
customThe residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 6% of methanol)

Sources & evidence

ORD record: ord-fd200b6995554252a89989f46e490c79
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658794B2

Reaction notes

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