Potassium Carbonate → HCID 59380310, compound

HRID 1483820Notes

Reaction equation

HRID 1483820 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.O1CCOCC1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>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].CC(=O)OCC.O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([F:18])[CH:24]=3)=[CH:3][N:4]=2)[N:7]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27339863-Fluorophenylboronic acidHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 59380310HCID 59380310, compoundYield 61.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (500 mg, 2.15 mmol) in a mixed solvent of dioxane (5 mL) and water (0.5 mL) was added (3-fluorophenyl)boronic acid (273 mg, 1.96 mmol), K2CO3 (811 mg, 5.88 mmol) and Pd(dppf)2Cl2 (79 mg, 0.098 mmol). The reaction mixture was stirred at 80° C. overnight under N2. TLC (PE:EA=5:1) showed the starting material was consumed. The mixture was cooled and concentrated. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc=20:1 to 1:1) to give 6-chloro-3-(3-fluorophenyl)imidazo[1,2-b]pyridazine (300 mg, 56%) as a yellow solid.

Workup

  1. customwas consumed
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (petroleum ether/EtOAc=20:1 to 1:1)

Sources & evidence

ORD record
ord-012fe408cb684072a2d63e0ed2e23772
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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