Dichloromethane → HCID 178476589, 화합물

HRID 245766노트

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HRID 245766 반응식
[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]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 178476587HCID 178476587, 화합물

생성물 1

HCID 178476589HCID 178476589, 화합물수율 97.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-fd200b6995554252a89989f46e490c79
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

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