تفاعل #1904046

ord-3f88218d47d6417394016e6ff5599050

معادلة التفاعل

Cc1ccccc1
toluene
OB(O)c1ccc(-n2c(-c3ccccc3)cc3ccccc32)cc1
4-(2-phenylindole-1-yl)phenyl boronic acid
Brc1ccc(-n2c3ccccc3c3ccccc32)cc1
9-(4-bromophenyl)carbazole
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
c1ccc(-c2cc3ccccc3n2-c2ccc(-c3ccc(-n4c5ccccc5c5ccccc54)cc3)cc2)cc1
4-(2-phenylindole-1-yl)-4′-(carbazole-9-yl)biphenyl
المردود 38.6%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThen, the mixture was refluxed
  2. 2
    workup.STIRRINGwith stirring for 5 hours under nitrogen flow
  3. 3
    درجة الحرارةthe reaction mixture was cooled to room temperature
  4. 4
    أخرىwas separated by filtration
  5. 5
    غسيلThe crystal was washed with acetone
  6. 6
    أخرىrecrystallized with a mixed solvent of toluene/ethanol
  7. 7
    أخرىcrystallize with methanol

الإجراء التجريبي

0.78 g (2.49 mmole) of 4-(2-phenylindole-1-yl)phenyl boronic acid and 0.80 g (2.48 mmole) of 9-(4-bromophenyl)carbazole were put in a 20 ml three-necked flask, and 2.5 ml of toluene, 1.5 ml of ethanol, and 2.5 ml of 2M-sodium carbonate solution were put therein, and 0.09 g (0.08 mmole) of tetrakis-(triphenylphosphine) palladium (0) was added under stirring at room temperature under nitrogen flow. Then, the mixture was refluxed with stirring for 5 hours under nitrogen flow. After the reaction was completed, the reaction mixture was cooled to room temperature and deposited crystal was separated by filtration. The crystal was washed with acetone and recrystallized with a mixed solvent of toluene/ethanol. The obtained crystal was refined by alumina column chromatography (eluent:toluene) and crystallize with methanol to give 0.49 g of a white crystal of 4-(2-phenylindole-1-yl)-4′-(carbazole-9-yl)biphenyl (Exemplary Compound No. 34)(yield: 38.6%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07597955B2uspto-grants-2009_10