Water → 12,12-Dimethyl-10,12-dihydroindeno[2,1-b]carbazole

HRID 719045

反応式

HRID 719045 の反応式
C[C:2]1(C)[C:14]2[CH:13]=[C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3Br)[CH:11]=C[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[C:24]([O-])(=O)[CH3:25].[K+].[CH3:29]N(C=O)C.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:29][C:24]1([CH3:25])[C:11]2[C:12]([N:15]=[C:16]3[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]3)=[CH:13][C:14]2[CH:2]=[C:3]3[C:8]([C:9]1=2)=[CH:7][CH2:6][CH:5]=[CH:4]3

参加物

7

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 517044Potassium AcetateHCID 86685013HCID 86685013、化合物

生成物 1

HCID 8668501212,12-Dimethyl-10,12-dihydroindeno[2,1-b]carbazole収率 55.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

N-(9,9-dimethyl-9H-fluorene-2-yl)-2-bromo-aniline (18.5 g), potassium acetate (6.98 g), and DMF (95 ml) were added to a nitrogen-substituted reaction vessel and aerated with nitrogen gas for 1 hour. The mixture was heated after adding tetrakis(triphenylphosphine)palladium (1.18 g) and stirred at 100° C. for 11 hours. After the mixture was cooled to a room temperature, the reaction liquid was added to water (300 ml) and extraction was performed with toluene (300 ml). An organic layer obtained was washed with water (200 ml) twice, dehydrated with anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel; eluent: toluene/n-hexane) to obtain a pale yellow powder of 12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole (7.9 g; yield 55.2%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureAfter the mixture was cooled to a room temperature
  3. customthe reaction liquid
  4. customAn organic layer obtained
  5. washwas washed with water (200 ml) twice
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a crude product
  8. customThe crude product was purified by column chromatography (carrier: silica gel; eluent: toluene/n-hexane)

出典と根拠

ORDレコード
ord-0e6eeb2eec1d4a5dbf2cf186ce8fc35b
出典データセット
uspto-grants-2015_11
特許番号
US09196837B2

関連ノート

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