Dichloromethane → HCID 58084636, compound

HRID 1517002Notes

Reaction equation

HRID 1517002 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[C:20]2[S:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:19]=2[CH:18]=[CH:17][CH:16]=1.CC([O-])(C)C.[Na+].ClCCl>C1(C)C(C)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH:18]1[C:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[S:21][C:20]=2[C:15]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 6854Carbazole2×HCID 4583524-BromodibenzothiopheneHCID 23676156Sodium t-butoxide

Product 1

HCID 58084636HCID 58084636, compoundYield 47.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst3×HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalyst3×HCID 7237O-XyleneSolvent

Procedure

A mixture of 9H-carbazole (10 g, 59.8 mmol), 4-bromodibenzo[b,d]thiophene (18.89 g, 71.8 mmol), and dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.982 g, 2.392 mmol) in 200 mL of Xylene was bubbled with N2 for 20 min. Pd2dba3 (0.548 g, 0.598 mmol) and sodium 2-methylpropan-2-olate (8.62 g, 90 mmol) were then added, and the mixture was heated to reflux under N2 for 24 h. TLC indicated the reaction did not go to completion. 0.3 g of Pd2(dba)3 and 0.6 g of dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine was added. The reaction was continued to reflux. The reaction was monitored by GC. After another 24 h, there was still carbazole starting material remaining. Again, 0.3 g of Pd2(dba)3 and 0.6 g of dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine were added. The reaction was refluxed again for 24 h. The reaction was stopped and worked up for purification. Column was used for purification. (1:3 dichloromethane:hexanes) 10 g (47.8% yield) of product was obtained.

Workup

  1. customwas bubbled with N2 for 20 min
  2. temperaturethe mixture was heated
  3. temperatureto reflux under N2 for 24 h
  4. temperatureto reflux
  5. temperatureThe reaction was refluxed again for 24 h
  6. customworked up for purification
  7. customColumn was used for purification

Sources & evidence

ORD record
ord-df463b3d9e59495582b2e3472201778e
Source dataset
uspto-grants-2012_07
Patent number
US08227801B2

Reaction notes

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