Dichloromethane → HCID 178476589、化合物

HRID 245766ノート

反応式

HRID 245766 の反応式
[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]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 178476587HCID 178476587、化合物

生成物 1

HCID 178476589HCID 178476589、化合物収率 97.6%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fd200b6995554252a89989f46e490c79
出典データセット
uspto-grants-2014_02
特許番号
US08658794B2

反応ノート

読み込み中…