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

HRID 1042576노트

반응식

HRID 1042576 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

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 (II) 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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e0f1c24a003941f29f0a64a778acece8
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557982B2

반응 노트

불러오는 중…