Dichloromethane → 3-Chloro-6-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyridazine

HRID 349237노트

반응식

HRID 349237 반응식
[Cl:1][C:2]1[N:3]=[N:4][C:5](I)=[CH:6][CH:7]=1.[CH2:9]([N:13]1[CH:17]=[CH:16][N:15]=[N:14]1)[CH2:10][C:11]#[CH:12].C(N(CC)CC)C.ClCCl>CN(C=O)C.[Cu](I)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>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:12]#[C:11][CH2:10][CH2:9][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 154188393-Chloro-6-iodopyridazineHCID 184535221-But-3-ynyl-1H-[1,2,3]triazole

생성물 1

HCID 860740673-Chloro-6-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyridazine

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

3-Chloro-6-iodo-pyridazine (11.56 g, 48.1 mmol), 1-but-3-ynyl-1H-[1,2,3]triazole (6.99 g, 57.7 mmol) and triethyl amine (NEt3) (94 ml) are dissolved in DMF (188 ml) and copper iodide (CuI) (0.981 g, 5.15 mmol) is added under stirring. After passing a stream of argon through the mixture for 10 min tetrakis(triphenylphosphine)palladium(0) (2.836 g, 2.43 mmol) is added and stirring is continued for 6 h at r.t. Dichloromethane (300 ml) is added, the mixture is washed with 0.5N hydrochloric acid (HCl) and brine, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate) yielding 3-chloro-6-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyridazine as a colorless solid. Yield 9.52 g (85%).

후처리

  1. customfor 10 min
  2. additionis added
  3. stirringstirring
  4. washthe mixture is washed with 0.5N hydrochloric acid (HCl) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-6c77992320494766b8912a493564a18b
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179812B2

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