N-phenyl-2-naphthylamine → HCID 58078267, compound

HRID 1852558Notes

Reaction equation

HRID 1852558 reaction equation
[Br:1][C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:19]1([NH:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC(O)=O.CC(O)=O.[Pd]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:16]3=[C:17]4[C:12](=[CH:11][CH:10]=[C:9]([N:25]([C:26]5[CH:35]=[CH:34][C:33]6[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=6)[CH:27]=5)[C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[C:8]4=[CH:7][CH:6]=2)[CH:13]=[CH:14][C:15]=13

Participants

6

Reactant 3

HCID 8679N-phenyl-2-naphthylamineHCID 176470Pyrene, 1,6-Dibromo-HCID 23676156Sodium t-butoxide

Product 1

HCID 58078267HCID 58078267, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 4144353Palladium (II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 18 g (50 mmol) of 1,6-dibromopyrene, 11 g (50 mmol) of N-phenylnaphthalen-2-amine, 0.16 g (0.7 mmol) of Pd(OAC)2, 0.5 g (1.4 mmole) of tri-tert-butylphosine, 6 g (75 mmol) sodium tert-butoxide was stirred in 200 ml dry toluene, the reaction mixture was then heat to 100° C. for about overnight under nitrogen. The solution was filtered. The toluene solution was removed under reduced pressure from the filtrate. The residue was extracted three times with dichloromethane and water, dried with MgSO4 and filtered, and the dichloromethane was removed under reduced pressure. The product was purified by column chromatography to get 9.2 g of product (yield 37%).

Workup

  1. filtrationThe solution was filtered
  2. customThe toluene solution was removed under reduced pressure from the filtrate
  3. extractionThe residue was extracted three times with dichloromethane and water
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customthe dichloromethane was removed under reduced pressure
  7. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-3236bfe73071403eb06e9252f592abf6
Source dataset
uspto-grants-2015_02
Patent number
US08962160B2

Reaction notes

Loading…