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Triethylamine → 6-[(4-Aminophenyl)ethynyl]imidazo[1,2-b]pyridazin-2-amine

HRID 589909
Notes
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Reaction equation

HRID 589909 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=2)[N:7]=1.[C:12]([C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)#[CH:13].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[NH2:18][C:17]1[CH:19]=[CH:20][C:14]([C:12]#[C:13][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=3)[N:7]=2)=[CH:15][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 37600254-EthynylanilineHCID 574410246-Iodoimidazo[1,2-B]pyridazin-2-amine

Product 1

HCID 1186384466-[(4-Aminophenyl)ethynyl]imidazo[1,2-b]pyridazin-2-amine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418476
HCID 178418476, compound
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To the mixture of 6-iodo-imidazo[1,2-b]pyridazin-2-ylamine (780 mg, 3.0 mmol, 1 eq) and 4-ethynylaniline (543 mg, 1.5 eq) in anhydrous DMF (10 mL) under nitrogen atmosphere was added triethylamine (1.67 mL, 4 eq), bis(triphenylphosphine)palladium(II) dichloride (210 mg, 0.1 eq) and copper(I) iodide (114 mg, 0.2 eq). After the reaction mixture was stirred at 50° C. for 30 minutes, it was partitioned between saturated aqueous sodium bicarbonate and chloroform (containing 3% v/v of MeOH). The organic layer was separated and washed with aqueous ammonium chloride, brine, and lastly dried with anhydrous sodium sulfate. The upper suspension mixture was decanted, concentrated, and the solid residue was subject to a gradient column chromatography (from CHCl3 to MeOH—CHCl3 1:30) to give 6-[(4-aminophenyl)ethynyl]imidazo[1,2-b]pyridazin-2-amine as a yellow solid in amount of 166 mg.

Workup

  1. customit was partitioned between saturated aqueous sodium bicarbonate and chloroform (
  2. additioncontaining 3% v/v of MeOH)
  3. customThe organic layer was separated
  4. washwashed with aqueous ammonium chloride, brine
  5. dry with materiallastly dried with anhydrous sodium sulfate
  6. customThe upper suspension mixture was decanted
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a7aa7a3cad184936abfc3a827735dd59
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09233968B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes