Potassium Phosphate, Tribasic → HCID 86676946, compound

HRID 2284376Notes

Reaction equation

HRID 2284376 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([C:9](I)=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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.O1CCOCC1>[Br:1][C:2]1[C:3]2[N:4]([C:9]([C:17]3[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=3)=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 86662987HCID 86662987, compound

Product 1

HCID 86676946HCID 86676946, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A pressure bottle charged with a mixture of 8-bromo-6-chloro-3-iodoimidazo[1,2-b]pyridazine (1.4 g, 3.91 mmol), 4-fluorophenylboronic acid (0.558 g, 3.98 mmol), dioxane (20 mL), and tetrakis(triphenylphosphine)palladium(0) (0.452 g, 0.39 mmol), and K3PO4 (2.49 g, 11.72 mmol) (2.0 M water solution) was stirred at room temperature for 5 min. under nitrogen. The resulting mixture was heated to 85° C. for 8 h. The reaction mixture was cooled to room temperature, quenched with water, and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by BIOTAGE® (0-20% EtOAc/CH2Cl2, 1.2 L) to give the product (0.56 g, 44%). LC/MS: Rt=3.22 min. LC/MS (Condition A): 325.83/327.83/329.83.

Workup

  1. temperatureThe resulting mixture was heated to 85° C. for 8 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with water
  4. additiondiluted with EtOAc
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc (3×20 mL)
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by BIOTAGE® (0-20% EtOAc/CH2Cl2, 1.2 L)

Sources & evidence

ORD record
ord-a22df00e157146b3b8bc152af12006cb
Source dataset
uspto-grants-2015_09
Patent number
US09145419B2

Reaction notes

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