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

HRID 589909

反応式

HRID 589909 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a7aa7a3cad184936abfc3a827735dd59
出典データセット
uspto-grants-2016_01
特許番号
US09233968B1

関連ノート

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