Pyrazole → HCID 86712410、化合物

HRID 628215ノート

反応式

HRID 628215 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]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH: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>ClCCl.[Cu]I.CS(C)=O>[C:4]1([N:5]2[C:6]3[CH:11]=[C:10]([N:21]4[CH:25]=[CH:24][CH:23]=[N:22]4)[CH:9]=[CH:8][C:7]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:12]=[CH:13][CH:14]=[CH:2][CH:3]=1

参加物

8

反応物 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 668380442-Bromo-9-phenyl-9H-carbazole

生成物 1

HCID 86712410HCID 86712410、化合物収率 45%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

A pressure vessel was charged with 2-bromo-9-phenyl-9H-carbazole (10 mmol), pyrazole (20 mmol), potassium carbonate (20 mmol), L-proline (2 mmol), copper(I) iodide (1 mmol), and dimethyl sulfoxide (25 mL). After three cycles of evacuation and backfilling with nitrogen, the vessel was sealed and stirred at 90° C. for three days. After cooling, the reaction mixture was diluted with dichloromethane (200 mL), washed four times with water (200 mL), and dried over magnesium sulfate. After removing the solvent under reduced pressure, the crude product was chromatographed over silica with hexane as the eluent, giving 9-phenyl-2-(1H-pyrazol-1-yl)-9H-carbazole in 45% yield.

後処理

  1. customAfter three cycles of evacuation and backfilling with nitrogen, the vessel was sealed
  2. temperatureAfter cooling
  3. washwashed four times with water (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. customAfter removing the solvent under reduced pressure
  6. customthe crude product was chromatographed over silica with hexane as the eluent

出典と根拠

ORDレコード
ord-e963c325a1ca47588ca1445589987a02
出典データセット
uspto-grants-2016_04
特許番号
US09312502B2

反応ノート

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