Dichloromethane → HCID 86583804, compound

HRID 2188239Notes

Reaction equation

HRID 2188239 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:23]2[C:28]([CH:29]=[C:30]3[C:35]=1[CH:34]=[CH:33][CH:32]=[CH:31]3)=[CH:27][CH:26]=[CH:25][CH:24]=2.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:24]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:23]2[C:28](=[CH:29][C:30]3[C:35]([CH:22]=2)=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 7106AcridanHCID 740629-BromoanthraceneHCID 23676156Sodium t-butoxide

Product 1

HCID 86583804HCID 86583804, compoundYield 72.9%

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 15.61 g of 9-bromoanthracene (60.7 mmol) in 100 mL of dry toluene was allowed to stir under inert atmosphere for 1 h. An additional 200 mL of toluene was added to the mixture and stirring was continued at room temperature for 30 min. The reaction mixture was poured into a mixture of 600 mL of CH2Cl2 and 100 g of silica gel. After stirring 15 min, the mixture was filtered, and the solid material was washed with an acditional 600 mL of CH2Cl2. The filtrate was concentrated in vacuo to afford a thick liquid, which was treated with 500 mL of hexanes. After stirring 15 min, the precipitate was collected by filtration, washed with 500 mL of hexanes, and dried. The solid was then triturated in 500 mL of hexanes for 1 h, filtered and dried to afford 14.39 g of N-anthracenylacridan by 1H-NMR analysis. The mother liquor was concentrated to a yellow solid which was trituratec in 300 mL of hexanes for 15 min. The precipitate was collected by filtration, washed with 200 mL of hexanes and dried to afford 5.40 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 19.79 g of the N-anthracenylacridan (100%).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 30 min
  3. stirringAfter stirring 15 min
  4. filtrationthe mixture was filtered
  5. washthe solid material was washed with an acditional 600 mL of CH2Cl2
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto afford a thick liquid, which
  8. stirringAfter stirring 15 min
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with 500 mL of hexanes
  11. customdried
  12. customThe solid was then triturated in 500 mL of hexanes for 1 h
  13. filtrationfiltered
  14. customdried

Sources & evidence

ORD record
ord-a77f18c8ecd1410b9e9df27b3ab54dd6
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

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