Anthracene → HCID 86696079, compound

HRID 921599Notes

Reaction equation

HRID 921599 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=3)[NH2:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:21]1[C:34]2[C:25](=[CH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:24]=[CH:23][CH:22]=1.C(O[Na])(C)(C)C>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].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C1(C)C=CC=CC=1>[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16]([NH:17][C:26]4[C:27]5[C:32]([CH:33]=[C:34]6[C:25]=4[CH:24]=[CH:23][CH:22]=[CH:21]6)=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:18]=[CH:19][CH:20]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 8418AnthraceneHCID 66874246HCID 66874246, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 86696079HCID 86696079, compoundYield 82.3%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Take 1.3 g of the carbazole from step (1c) above (0.005M) in glove box and add 2.3 g anthracene from step (a) above (0.005M). Add 0.05 g Pd2DBA3 (0.05 mM), 0.022 g P(t-Bu)3 (0.11 mM) and 0.55 g t-BuONa and dissolve all into 25 mL toluene. Upon addition of catalyst materials, there is a mild exotherm. Heat in glove box in mantle at 80 C. under nitrogen for 2 hr as a dark brown solution (thick). Cool and work up by basic-alumina chromatography eluting with DCM and collect dark yellow solution with bright purple/blue PL. Evap to a very dark oily solid. Wash with methanol to give a nice powdery yellow solid. Rinse recovered solid with methanol to give ˜1.8 g of yellow solid. The structure was confirmed by 1-H nmr spectroscopy.

Workup

  1. additionUpon addition of catalyst materials, there
  2. temperatureHeat in glove box in mantle at 80 C
  3. temperatureCool
  4. washeluting with DCM
  5. customcollect dark yellow solution with bright purple/blue PL
  6. washWash with methanol
  7. customto give a nice powdery yellow solid
  8. washRinse
  9. customrecovered solid with methanol

Sources & evidence

ORD record
ord-ee93d13dce2e4a8294e1bb1d42170c21
Source dataset
uspto-grants-2016_03
Patent number
US09276217B2

Reaction notes

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