Pyrazole → 2-(1H-pyrazol-1-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole

HRID 591583ノート

反応式

HRID 591583 の反応式
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[C:4]=2[CH:3]=1.[NH:21]1[CH:25]=[CH:24][CH:23]=[N:22]1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>[Cu]I>[N:21]1([C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]([CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][O:16]4)[C:4]=3[CH:3]=2)[CH:25]=[CH:24][CH:23]=[N:22]1

参加物

6

反応物 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 177606792-bromo-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole

生成物 1

HCID 710606072-(1H-pyrazol-1-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole収率 40%

試薬・触媒・溶媒 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒

反応条件

温度
90 °C

実験手順

Under a nitrogen atmosphere, 10 mmol of 2-bromo-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole, 15 mmol of pyrazole, 1 mmol of copper(I)iodide, 25 mmol of potassium carbonate, and 2 mmol of L-proline were combined in 25 mL of stirring degassed dimethyl sulfoxide. The mixture was heated to 90° C. for 3 days before being cooled and separated between dichloromethane and water. The water layer was washed twice with dichloromethane and the organics were combined and washed once with brine. The organic fraction was dried with magnesium sulfate and concentrated under reduced pressure and subjected to column chromatography of silica with dichloromethane as the eluent. After concentrating under reduced pressure, 2-(1H-pyrazol-1-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole was isolated in a 40% yield.

後処理

  1. customdegassed dimethyl sulfoxide
  2. temperaturebefore being cooled
  3. customseparated between dichloromethane and water
  4. washThe water layer was washed twice with dichloromethane
  5. washwashed once with brine
  6. dry with materialThe organic fraction was dried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. concentrationAfter concentrating under reduced pressure

出典と根拠

ORDレコード
ord-a8647f4ff43448d8a79412c80779f585
出典データセット
uspto-grants-2016_01
特許番号
US09238668B2

反応ノート

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