Potassium Phosphate, Tribasic → HCID 117818114, compound

HRID 634546Notes

Reaction equation

HRID 634546 reaction equation
[C:1]1([N:7]([C:21]2[CH:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:23][CH:22]=2)[C:8]2[CH:20]=[CH:19][C:11]3[O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:37]1[CH:38]=[CH:39][C:40]2[NH:41][C:42]3[C:47]([C:48]=2[CH:49]=1)=[CH:46][CH:45]=[CH:44][CH:43]=3.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(O)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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:39]1[C:40]2[NH:41][C:42]3[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:48]=2[CH:49]=[C:37]([C:24]2[CH:23]=[CH:22][C:21]([N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]3[CH:20]=[CH:19][C:11]4[O:12][C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=5[C:10]=4[CH:9]=3)=[CH:26][CH:25]=2)[CH:38]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2524463-BromocarbazoleHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 123860128HCID 123860128, compound

Product 1

HCID 117818114HCID 117818114, compoundYield 85.6%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)dibenzo[b,d]furan-2-amine (3.25 g, 7.0 mol), and 3-bromo-9H-carbazole (1.73 g, 7.0 mmol) were mixed in 45 mL of toluene and 15 ml of ethanol. To the solution was bubbled with nitrogen for 15 min. Pd2(dba)3 (0.16 g, 0.18 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.29 g, 7.0 mmol) and K3PO4 (4.49 g, 21.1 mmol) were added. The mixture was refluxed overnight under nitrogen. After cooling, aqueous layer was removed from the reaction mixture and dry over magnesium sulfate, and was filtered through filter paper and the filtrate was then evaporated. The residue was then purified by column chromatography using THF:hexane (1:3, v/v) as eluent 3.0 g (85%) of a white solid was obtained as the product.

Workup

  1. customTo the solution was bubbled with nitrogen for 15 min
  2. temperatureThe mixture was refluxed overnight under nitrogen
  3. temperatureAfter cooling
  4. customaqueous layer was removed from the reaction mixture
  5. dry with materialdry over magnesium sulfate
  6. filtrationwas filtered
  7. filtrationthrough filter paper
  8. customthe filtrate was then evaporated
  9. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-001e166b462e477db91cbf3cb9679c51
Source dataset
uspto-grants-2016_04
Patent number
US09324949B2

Reaction notes

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