Dichloromethane → HCID 86583805, compound

HRID 2188240Notes

Reaction equation

HRID 2188240 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].Br[C:22]1[C:35]2[C:36]3=[C:37]4[C:32](=[CH:33][CH:34]=2)[CH:31]=[CH:30][CH:29]=[C:28]4[CH:27]=[CH:26][C:25]3=[CH:24][CH:23]=1.C(Cl)Cl>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:29]1([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)[C:28]2[C:37]3=[C:36]4[C:25](=[CH:26][CH:27]=2)[CH:24]=[CH:23][CH:22]=[C:35]4[CH:34]=[CH:33][C:32]3=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 7106AcridanHCID 1596271-BromopyreneHCID 23676156Sodium t-butoxide

Product 1

HCID 86583805HCID 86583805, compoundYield 60.3%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Procedure

A mixture of 10.00 g of acridan (55.2 mmol), 247.7 mg of Pd(OAc)2 (1.10 mmol), 178.6 mg of tri-t-butylphosphine (0.88 mmol), 7.95 g of sodium t-butoxide (82.7 mmol), and 17.06 g of 1-bromopyrene (60.7 mmol) in 100 mL of dry toluene was allowed to stir under inert atmosphere. The exothermic reaction heated to reflux, causing a precipitate to form. An additional 200 mL of toluene was added to the mixture and stirring was continued at room temperature for 1 h. The reaction mixture was poured into a mixture of 600 mL of CH2Cl2 and 100 g of silica gel. The mixture was filtered, and the solid material was washed with 600 mL of CH2Cl2. The filtrate was concentrated in vacuo to afford a thick liquid containing a precipitate. The precipitate was collected by filtration, washed with 300 mL of toluene and 500 mL of hexanes, and dried to afford 12.69 g of N-pyrenylacridan by 1H-NMR analysis. The mother liquor was concentrated to a yellow solid which was triturated in 300 mL of hexanes for 30 min. The precipitate was collected by filtration, washed with 200 mL of hexanes and dried to afford 7.46 g of solid. 1H-NMR analysis showed the second crop of product was slightly less pure than the first. The two lots were combined to afford 20.15 g of the N-pyrenylacridan (95.7%).

Workup

  1. customThe exothermic reaction
  2. temperatureheated
  3. temperatureto reflux
  4. customto form
  5. stirringstirring
  6. filtrationThe mixture was filtered
  7. washthe solid material was washed with 600 mL of CH2Cl2
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto afford a thick liquid
  10. additioncontaining a precipitate
  11. filtrationThe precipitate was collected by filtration
  12. washwashed with 300 mL of toluene and 500 mL of hexanes
  13. customdried

Sources & evidence

ORD record
ord-2923f2f85fa94382a3cc18112a7e20e2
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

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