Potassium Carbonate → HCID 58857788, compound

HRID 1483798Notes

Reaction equation

HRID 1483798 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.[C:12]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)#[N:13].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>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:18]3[CH:19]=[C:14]([CH:15]=[CH:16][CH:17]=3)[C:12]#[N:13])=[CH:3][N:4]=2)[N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 58857788HCID 58857788, compoundYield 55%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (2 g, 8.6 mmol) and 3-(cyano)phenylboronic acid (1.26 g, 8.6 mmol) in dioxane/H2O (100 mL, 4:1) was added K2CO3 (2.38 g, 17.2 mmol) and Pd(PPh3)4 (0.19 g, 0.172 mmol), the mixture was stirred at 110° C. for 3 h. The solution was concentrated and partitioned in EtOAc/H2O. The aqueous layer was washed with EtOAc (50 mL) 3 times. The collected organic layers were dried over Na2SO4, concentrated and purified by column chromatography to give compound 3-(6-chloroimidazo[1,2-b]pyridazin-3-yl)benzonitrile (1.2 g, 4.71 mmol, yield 55%) as a brown solid.

Workup

  1. concentrationThe solution was concentrated
  2. custompartitioned in EtOAc/H2O
  3. washThe aqueous layer was washed with EtOAc (50 mL) 3 times
  4. dry with materialThe collected organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-45a9ee11fdf049379bfb89ba3ea672c8
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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