Cesium carbonate → HCID 86704332, compound

HRID 1397829Notes

Reaction equation

HRID 1397829 reaction equation
FC(F)(F)[C:3]1[N:16]=[C:15]2[C:17]3=[C:18]4[C:8]([N:9]=[C:10](C(F)(F)F)[N:11]=[C:12]4[CH:13]=[C:14]2Br)=[C:7](Br)[CH:6]=[C:5]3[N:4]=1.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:27][C:28]([F:39])([F:38])[C:29]1[CH:34]=[CH:33][C:32]([C:7]2[C:8]3[C:18]4[C:12](=[CH:13][C:14]([C:32]5[CH:33]=[CH:34][C:29]([C:28]([F:39])([F:38])[F:27])=[CH:30][CH:31]=5)=[C:15]5[C:17]=4[C:5]([CH:6]=2)=[N:4][CH:3]=[N:16]5)[N:11]=[CH:10][N:9]=3)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 60202001HCID 60202001, compound

Product 1

HCID 86704332HCID 86704332, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
101 °C

Procedure

An oven-dried Schlenk tube was loaded with 130 mg (0.26 mmol) 2,7-bis-(trifluoromethyl)-4,9-dibromo-1,3,6,8-tetraazapyrene, 197 mg (1.04 mmol) 4-trifluoromethylphenylboronic acid, 508 mg (1.56 mmol) caesium carbonate and 19 mg (0.03 mmol) Pd(dppf)Cl2 and evacuated and refilled with argon for three times. 20 ml abs. 1,4-dioxane were added, the Schlenk tube was sealed with a glass cap and the reaction mixture was stirred at 101° C. for 48 h. The mixture was allowed to cool to room temperature, the solvent was evaporated and the solid residue was extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and evaporated in vacuo. The solid was washed with methanol and pentane to yield 35 mg (0.06 mmol, 23%) of the compound as a white solid.

Workup

  1. customevacuated
  2. additionrefilled with argon for three times
  3. addition1,4-dioxane were added
  4. customthe Schlenk tube was sealed with a glass
  5. customcap
  6. temperatureto cool to room temperature
  7. customthe solvent was evaporated
  8. extractionthe solid residue was extracted with chloroform
  9. washThe organic phase was washed with water and brine
  10. dry with materialdried over sodium sulphate
  11. customevaporated in vacuo
  12. washThe solid was washed with methanol and pentane

Sources & evidence

ORD record
ord-fc9a27076945446ca3e1cf58ca3ebef4
Source dataset
uspto-grants-2014_12
Patent number
US08901300B2

Reaction notes

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