Potassium Carbonate → HCID 58281901, compound

HRID 1425494Notes

Reaction equation

HRID 1425494 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]2[CH:21]=[CH:20][C:19](B3OC(C)(C)C(C)(C)O3)=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:31][C:32]1[CH:37]=[CH:36][C:35](I)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[Br:31][C:32]1[CH:37]=[CH:36][C:35]([C:19]2[CH:18]=[CH:17][C:16]([C:8]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=3)=[CH:21][CH:20]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 59629070HCID 59629070, compound

Product 1

HCID 58281901HCID 58281901, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
95 °C

Procedure

A mixture of compound 3 (4.01 g, 10.1 mmol), 1-bromo-4-iodobenzene (5.73 g, 20.2 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol) and potassium carbonate (4.2 g, 30 mmol) in dioxane/water (60 ml/10 ml) was degassed and heated at 95° C. overnight. After being cooled to RT, the mixture was filtered to collect the precipitate, which was redissolved in hot dichloromethane. The dichloromethane solution was filtered and concentrated with presence of methanol until a large amount of white precipitate forms. Filtration and drying in air gave a white solid (2.58 g, in 60% yield).

Workup

  1. customwas degassed
  2. temperatureAfter being cooled to RT
  3. filtrationthe mixture was filtered
  4. customto collect the precipitate, which
  5. dissolutionwas redissolved in hot dichloromethane
  6. filtrationThe dichloromethane solution was filtered
  7. concentrationconcentrated with presence of methanol until a large amount of white precipitate forms
  8. filtrationFiltration
  9. customdrying in air
  10. customgave a white solid (2.58 g, in 60% yield)

Sources & evidence

ORD record
ord-7435f8a6d5324517a376b0e608a9d643
Source dataset
uspto-grants-2015_01
Patent number
US08929978B2

Reaction notes

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