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

HRID 349237ノート

反応式

HRID 349237 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-6c77992320494766b8912a493564a18b
出典データセット
uspto-grants-2007_02
特許番号
US07179812B2

反応ノート

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