Water → 3-(4-Chloro-phenyl)-6-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridazin

HRID 1916543ノート

反応式

HRID 1916543 の反応式
C(N(CC)CC)C.Cl[C:9]1[N:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1.[CH2:22]([C:26]1[CH:37]=[CH:36][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:28][CH:27]=1)[CH2:23][C:24]#[CH:25].O>CN(C=O)C.[Cu]I>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:11]=[N:10][C:9]([C:25]#[C:24][CH2:23][CH2:22][C:26]3[CH:37]=[CH:36][C:29]([CH2:30][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:28][CH:27]=3)=[CH:14][CH:13]=2)=[CH:16][CH:17]=1

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 122575023-Chloro-6-(4-chlorophenyl)pyridazineHCID 859698431-(4-But-3-ynyl-benzyl)-pyrrolidine

生成物 1

HCID 100924723-(4-Chloro-phenyl)-6-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridazin

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Under an argon atmosphere 0.1 mL (0.72 mmol) triethylamine, 3 mg (0.02 mmol) CuI and 8 mg (0.01 mmol) bis-triphenylphosphane-palladium(II)-chloride are added to a solution of 77 mg (0.34 mmol) 3-chloro-6-(4-chloro-phenyl)-pyridazine and 73 mg (0.34 mmol) 1-(4-but-3-ynyl-benzyl)-pyrrolidine (Example 2e) in 4 mL DMF and the reaction mixture is stirred for 20 min at 100° C. and at 300 W in the microwave. The reaction mixture is combined with 10 mL water, extracted with 10 mL EtOAc and the organic phase is washed with water and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:1).

後処理

  1. extractionextracted with 10 mL EtOAc
  2. washthe organic phase is washed with water
  3. dry with materialdried over Na2SO4
  4. customis purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:1)

出典と根拠

ORDレコード
ord-05ee01884f09455dbae81d294c7d2f37
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

反応ノート

読み込み中…