Triethylamine → 5-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-2-methyl-2H-pyridazin-3-one

HRID 2194410ノート

反応式

HRID 2194410 の反応式
I[C:2]1[N:3]=[C:4]([CH3:15])[N:5]([C:7]2[CH:12]=[N:11][N:10]([CH3:13])[C:9](=[O:14])[CH:8]=2)[CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[Cl:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([C:49]#[CH:50])[CH:44]=1>[Cu]I>[Cl:42][C:43]1[CH:44]=[C:45]([C:49]#[C:50][C:2]2[N:3]=[C:4]([CH3:15])[N:5]([C:7]3[CH:12]=[N:11][N:10]([CH3:13])[C:9](=[O:14])[CH:8]=3)[CH:6]=2)[CH:46]=[CH:47][CH:48]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 1230861-Chloro-3-ethynylbenzeneHCID 668656855-(4-iodo-2-methyl-imidazol-1-yl)-2-methyl-2H-pyridazin-3-one

生成物 1

HCID 498727675-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-2-methyl-2H-pyridazin-3-one収率 67.3%

試薬・触媒・溶媒 1

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

実験手順

A solution of 8 mg bis(triphenyl-phosphine)palladium dichloride in 3 ml of DMF was degassed with argon. Then 52 mg (0.165 mmol) 5-(4-iodo-2-methyl-imidazol-1-yl)-2-methyl-2H-pyridazin-3-one, 1 mg (0.03 mmol) of triphenylphosphine, 0.046 ml (0.33 mmol) triethylamine were added and the mixture was stirred for 5 min at room temperature. Then 1 mg (0.005 mmol) of copper(I) iodide and 0.042 ml (0.33 mmol) of 1-chloro-3-ethynyl-benzene were added and the mixture was stirred for 2 h at 50° C. The mixture was evaporated to dryness in vaccuo, taken up in 5 ml of ethyl acetate. Then ca. 1 g of silicagel was added and the suspension was evaporated to dryness. The silicagel containing adsorbed product was loaded onto a 20 g flash chromatography column. The product was eluted with ethyl acetate. The pure fractions were concentrated to yield 36 mg (0.111 mmol, 67%) of the title compound as a light yellow crystalline solid, MS: m/e=325.2, 327.2 (M+H+).

後処理

  1. customA solution of 8 mg bis(triphenyl-phosphine)palladium dichloride in 3 ml of DMF was degassed with argon
  2. stirringthe mixture was stirred for 2 h at 50° C
  3. customThe mixture was evaporated to dryness in vaccuo
  4. additionThen ca. 1 g of silicagel was added
  5. customthe suspension was evaporated to dryness
  6. additionThe silicagel containing adsorbed product
  7. washThe product was eluted with ethyl acetate
  8. concentrationThe pure fractions were concentrated

出典と根拠

ORDレコード
ord-9456904677ea4a209e8933f90b9186fb
出典データセット
uspto-grants-2012_12
特許番号
US08334287B2

反応ノート

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