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

HRID 719045

Reaction equation

HRID 719045 reaction equation
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

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 517044Potassium AcetateHCID 86685013N-(9,9-dimethylfluoren-2-yl)-2-bromoaniline

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-0e6eeb2eec1d4a5dbf2cf186ce8fc35b
Source dataset
uspto-grants-2015_11
Patent number
US09196837B2

Linked notes

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