Triphenylsilane → HCID 86676047, compound

HRID 1502195Notes

Reaction equation

HRID 1502195 reaction equation
[C:1]([N:4]1[C:16]2[CH:15]=[CH:14][C:13](I)=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[C:8](I)[CH:9]=2)(=[O:3])[CH3:2].[C:19]1([SiH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN1CCCC1=O>[C:1]([N:4]1[C:16]2[CH:15]=[CH:14][C:13]([Si:25]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]([Si:25]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:9]=2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 69922TriphenylsilaneHCID 134073501-(3,6-Diiodo-9H-carbazol-9-yl)ethan-1-one

Product 1

HCID 86676047HCID 86676047, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

9-Acetyl-3,6-diiodocarbazole (10.0 g) and triphenylsilane (12.4 g) were dry N-methylpyrrolidone (200 mL), followed by bubbling with argon gas for 30 min. Tripotassium phosphate (27.6 g) and bis(tri-t-butylphosphine)palladium (0.111 g) were added thereto, and the mixture was stirred at room temperature for 19 hours. The obtained reaction mixture was filtrated, and the filtrate was extracted with methylene chloride. The separated organic layer was washed with brine and dried, and the methylene chloride was evaporated. The residue was treated through silica gel column chromatography (eluent: toluene), to thereby obtain 1.97 g of 9-acetyl-3,6-bis(triphenylsilyl)carbazole as colorless powder.

Workup

  1. customby bubbling with argon gas for 30 min
  2. additionTripotassium phosphate (27.6 g) and bis(tri-t-butylphosphine)palladium (0.111 g) were added
  3. customThe obtained reaction mixture
  4. filtrationwas filtrated
  5. extractionthe filtrate was extracted with methylene chloride
  6. washThe separated organic layer was washed with brine
  7. customdried
  8. customthe methylene chloride was evaporated
  9. additionThe residue was treated through silica gel column chromatography (eluent: toluene)

Sources & evidence

ORD record
ord-b48214e5483042ad85a7dc9f8dd92e0d
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Reaction notes

Loading…