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3-Bromo-6-chloroimidazo(1,2-b)pyridazine → 6-Chloro-3-(3-methoxypyridazin-4-yl)imidazo[1,2-b]pyridazine

HRID 2279068
Notes
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Reaction equation

HRID 2279068 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.[CH3:12][O:13][C:14]1[N:15]=[N:16][CH:17]=[CH:18][C:19]=1[Sn](CCCC)(CCCC)CCCC>[Cu]I.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.CN(C=O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:19]3[CH:18]=[CH:17][N:16]=[N:15][C:14]=3[O:13][CH3:12])=[CH:3][N:4]=2)[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 674857293-Methoxy-4-(tributylstannyl)pyridazine

Product 1

HCID 867023276-Chloro-3-(3-methoxypyridazin-4-yl)imidazo[1,2-b]pyridazineYield 64.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (Preparation 1b, 182 mg, 0.78 mmol), 3-methoxy-4-(tributylstannyl)pyridazine (Preparation 8b, 313 mg, 0.78 mmol), copper(I) iodide (15 mg, 0.08 mmol) and dry N,N′-dimethylformamide (4 mL) in a Schlenk vial was subjected to three cycles of evacuation backfilling with argon. Tetrakis(triphenylphosphine)palladium(0) (91 mg, 0.08 mmol) was then added and the resulting mixture was subjected to three further cycles of evacuation backfilling with argon before being stirred at 100° C. for 20 hours. The reaction mixture was cooled down, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (1:1 hexanes/ethyl acetate to 100% ethyl acetate) to give the title compound (131 mg, 64%) as a beige solid.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography (1:1 hexanes/ethyl acetate to 100% ethyl acetate)

Sources & evidence

ORD record
ord-6d5d64b71fbf48d6a37a2caf250cbbf9
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133200B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes