Tetraethylammonium Hydroxide → HCID 23509207, compound

HRID 870114Notes

Reaction equation

HRID 870114 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2[C:20]3[NH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].C([N+]([CH2:29][CH3:30])(CC)CC)C>CC(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>[C:30]1([C:9]2[CH:10]=[CH:11][C:12]3[C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[NH:19][C:20]=3[C:8]=2[C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=2)[CH:29]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 6509Tetraethylammonium HydroxideHCID 670514083-Iodophenylcarbazole

Product 1

HCID 23509207HCID 23509207, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

91 g (242 mmol) of 3-iodophenylcarbazole 18 and 91 g (246 mmol) of phenylcarbazoleboronic ester 19 are suspended in acetone, and a 350 ml of 20% tetraethylammonium hydroxide solution (493 mmol) are added, the mixture is carefully degassed using argon. 4.6 g (4 mmol) of tetrakistriphenylphosphinepalladium are subsequently added. The reaction is heated to 70° C. The progress of the reaction is followed by means of thin-layer chromatography. When the reaction is complete, the batch is cooled to room temperature, and the precipitated product is filtered off with suction. The crude product is recrystallised from acetonitrile, giving a beige solid.

Workup

  1. customthe mixture is carefully degassed
  2. temperaturethe batch is cooled to room temperature
  3. filtrationthe precipitated product is filtered off with suction
  4. customThe crude product is recrystallised from acetonitrile
  5. customgiving a beige solid

Sources & evidence

ORD record
ord-59a89d23f42d4958b1c57e05f65863fd
Source dataset
uspto-grants-2015_03
Patent number
US08969512B2

Reaction notes

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