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

HRID 589909

반응식

HRID 589909 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a7aa7a3cad184936abfc3a827735dd59
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233968B1

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