Nitrogen → Dimethyl 4'-(bisbiphenyl-4-ylamino)-4-carbazol-9-ylbiphenyl-2,5-dicarboxylate

HRID 1485598Notes

Reaction equation

HRID 1485598 reaction equation
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([N:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.Br[C:36]1[CH:45]=[C:44]([C:46]([O:48][CH3:49])=[O:47])[C:43]([N:50]2[C:62]3[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=3[C:56]3[C:51]2=[CH:52][CH:53]=[CH:54][CH:55]=3)=[CH:42][C:37]=1[C:38]([O:40][CH3:41])=[O:39].C(=O)([O-])[O-].[K+].[K+].N#N>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO>[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([N:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:36]3[C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:42][C:43]([N:50]4[C:62]5[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=5[C:56]5[C:51]4=[CH:52][CH:53]=[CH:54][CH:55]=5)=[C:44]([C:46]([O:48][CH3:49])=[O:47])[CH:45]=3)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 57746383(4-(Di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acidHCID 67450647Dimethyl 2-bromo-5-carbazol-9-ylterephthalate

Product 1

HCID 67451273Dimethyl 4'-(bisbiphenyl-4-ylamino)-4-carbazol-9-ylbiphenyl-2,5-dicarboxylate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

91 g (207 mol) of bisbiphenyl-4-yl-(4-boronophenyl)amine, 207 g (474 mmol) of dimethyl 2-bromo-5-carbazol-9-ylterephthalate and 315.9 g (2.29 mol) of potassium carbonate are initially introduced in a mixture of 850 ml of toluene and 850 ml of water and saturated with N2 for 30 min. After addition of 1.36 g (1.18 mmol) of Pd(PPh3)4, the mixture is heated at the boil for 4 h. After cooling to RT and addition of 400 ml of EtOH, the mixture is cooled to room temperature and stirred for 1 h, and the precipitate is filtered off with suction, washed with water, EtOH and heptane and dried at 80° C. in vacuo. The yield is 254 g (336 mmol), corresponding to 72% of theory.

Workup

  1. temperaturethe mixture is heated at the boil for 4 h
  2. temperaturethe mixture is cooled to room temperature
  3. filtrationthe precipitate is filtered off with suction
  4. washwashed with water, EtOH and heptane
  5. customdried at 80° C. in vacuo

Sources & evidence

ORD record
ord-93cdc00cf0b54f0f841f4f62c9e1c0a2
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

Loading…