Potassium Carbonate → HCID 86677000, compound

HRID 1473737Notes

Reaction equation

HRID 1473737 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][C:10]2[C:31]3[C:19](=[CH:20][C:21]4[N:22]([CH2:32][CH3:33])[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=5[C:29]=4[CH:30]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:11]=2[CH:12]=1)(=O)=O.[C:36]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:41]=[CH:40][C:39]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[CH:45][CH:44]=2)=[CH:38][CH:37]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:46]1([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:45]=[CH:44][C:43]([N:42]([C:39]2[CH:40]=[CH:41][C:36]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[CH:37][CH:38]=2)[C:7]2[CH:8]=[CH:9][C:10]3[C:31]4[C:19](=[CH:20][C:21]5[N:22]([CH2:32][CH3:33])[C:23]6[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=6[C:29]=5[CH:30]=4)[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:11]=3[CH:12]=2)=[CH:48][CH:47]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 504244Bis-biphenyl-4-yl-amineHCID 86677001HCID 86677001, compound

Product 1

HCID 86677000HCID 86677000, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

2.69 g (5.46 mmol) of 10-ethyl-10H-phenanthro[9,10-b]carbazol-3-yl trifluoromethanesulfonate synthesized in Synthetic Example 9, 2.63 g (8.18 mmol) of dibiphenyl-4-ylamine, 0.04 g (0.16 mmol) of Pd(OAc)2, 0.20 g (0.33 mmol) of Binap, and 1.51 g (10.91 mmol) of K2CO3 were put, suspended in 30 ml of toluene, and refluxed and agitated for 12 hours. After the reaction was finished, extraction was performed by dichloromethane, filtering was performed by silica gel, and the column was used at a ratio of hexane:MC=4:1 (v/v) to obtain 2.83 g of N,N-di(biphenyl-4-yl)-10-ethyl-10H-phenanthro[9,10-b]carbazol-3-amine that was the target compound (yield 78%).

Workup

  1. temperaturerefluxed
  2. extractionextraction
  3. filtrationfiltering

Sources & evidence

ORD record
ord-2392331059b448a78c7943ee9e543bc8
Source dataset
uspto-grants-2015_04
Patent number
US09017829B2

Reaction notes

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