Tris(1,1-dimethylethyl)phosphine → 9-(4-[Benzoxazol-2-yl)phenyl]-3,6-diphenyl-9H-carbazole

HRID 1028870Notes

Reaction equation

HRID 1028870 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:17]1([C:23]2[CH:24]=[CH:25][C:26]3[NH:27][C:28]4[C:33]([C:34]=3[CH:35]=2)=[CH:32][C:31]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:30][CH:29]=4)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1.CCCCCC>[O:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([N:27]2[C:28]3[CH:29]=[CH:30][C:31]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:32][C:33]=3[C:34]3[C:26]2=[CH:25][CH:24]=[C:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:35]=3)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 31232953,6-DiphenylcarbazoleHCID 128467152-(4-Bromophenyl)benzo(d)oxazoleHCID 23676156Sodium t-butoxide

Product 1

HCID 582817999-(4-[Benzoxazol-2-yl)phenyl]-3,6-diphenyl-9H-carbazole

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

In a 100 mL three-neck flask were put 1.0 g (3.7 mmol) of 2-(4-bromophenyl)benzoxazole, 1.2 g (3.7 mmol) of 3,6-diphenyl-9H-carbazole, and 0.77 g (8.0 mmol) of sodium tert-butoxide. The atmosphere in the flask was replaced with nitrogen. To this mixture were added 15 mL of toluene and 0.10 mL of a 10% hexane solution of tri(tert-butyl)phosphine. This mixture was degassed by reducing the pressure in the flask by using an aspirator. After that, the atmosphere in the flask was replaced with nitrogen. To this mixture was added 0.030 g (0.052 mmol) of bis (dibenzylideneacetone)palladium(0), followed by stirring under a nitrogen stream at 80° C. for 5 hours. After that, toluene was added to this mixture, and this suspension was suction filtered through Celite 545 (produced by Kishida Chemical Co., Ltd., Catalog No. 020-14815), whereby a filtrate was obtained.

Workup

  1. customIn a 100 mL three-neck flask were put
  2. customThis mixture was degassed
  3. filtrationfiltered through Celite 545 (produced by Kishida Chemical Co., Ltd., Catalog No. 020-14815), whereby a filtrate
  4. customwas obtained

Sources & evidence

ORD record
ord-b67aa0056f514279bad981628d21f93c
Source dataset
uspto-grants-2014_05
Patent number
US08735597B2

Reaction notes

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