Acetonitrile → 4-(2,4-Dimethoxy-3-nitro-phenylethynyl)-1-methyl-1H-pyrazole

HRID 2059612ノート

反応式

HRID 2059612 の反応式
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7]([O:12][CH3:13])[CH:6]=[CH:5][C:4]=1I.[C:15]([C:17]1[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=1)#[CH:16].C(#N)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.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7]([O:12][CH3:13])[CH:6]=[CH:5][C:4]=1[C:16]#[C:15][C:17]1[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=1

参加物

7

反応物 3

HCID 6342AcetonitrileHCID 511383214-Ethynyl-1-methyl-1H-pyrazoleHCID 574219462,4-Dimethoxy-3-nitro-iodobenzene

生成物 1

HCID 687741874-(2,4-Dimethoxy-3-nitro-phenylethynyl)-1-methyl-1H-pyrazole収率 71%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

To a mixture of 2,4-dimethoxy-3-nitro-iodobenzene (0.95 mmol), 0.122 g (1.15 mmol) of 4-ethynyl-1-methyl-1H-pyrazole, 0.028 g (0.04 mmol) of dichlorobis (triphenylphosphine)palladium (H) and 8 mg (0.042 mmol) of copper (I) iodide 4 mL of anhydrous acetonitrile and 2 mL of triethylamine were added under nitrogen atmosphere at room temperature. The resulting mixture was stirred for 1 hour, when TLC indicated a consumption of the iodobenzene. The solvent was evaporated under reduced pressure and the residue purified by flash column chromatography (silica gel; dichloromethane:ethyl acetate 9:1) to give the title compound in 71% yield as creamy crystals. H1 NMR (CDCl3) 3.88(s, 3H, Me); 3.9 (s, 3H, OMe); 4.07 (s, 3H, OMe); 6.7 (d, 1H, CH, J=8.9 Hz); 7.44 (d, 1H, CH, J=8.9 Hz); 7.56 (s, 1H, CH pyr); 7.62 (s, 1H, CH pyr).

後処理

  1. additionwere added under nitrogen atmosphere at room temperature
  2. customa consumption of the iodobenzene
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue purified by flash column chromatography (silica gel; dichloromethane:ethyl acetate 9:1)

出典と根拠

ORDレコード
ord-1b97c8df0a304ae1a3a6be24f0a12dcc
出典データセット
uspto-grants-2012_10
特許番号
US08278290B2

反応ノート

読み込み中…