Sodium Iodide → methyl 4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]-3-isopropoxybenzoate

HRID 507983노트

반응식

HRID 507983 반응식
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[I-].[Na+].Br[CH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=1[O:34][CH:35]([CH3:37])[CH3:36]>CN(C)C=O.C(OCC)(=O)C>[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=3[O:34][CH:35]([CH3:37])[CH3:36])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 708401H-Pyrazole, 3,5-diphenyl-HCID 23157338HCID 23157338, 화합물

생성물 1

HCID 23157367methyl 4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]-3-isopropoxybenzoate수율 92.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3,5-diphenyl-1H-pyrazole (0.36 g, 1.65 mmol) in N,N-dimethylformamide (8.6 mL) was added sodium hydride (60% in oil, 66 mg, 1.65 mmol) under stirring at room temperature, and the mixture was stirred at the same temperature for 30 min. To the reaction mixture was added sodium iodide (22 mg, 0.15 mmol) and a solution of methyl 4-(bromomethyl)-3-isopropoxybenzoate (0.43 g, 1.50 mmol) in N,N-dimethylformamide (4.3 mL), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1) to give the title compound (0.59 g, yield 92%) as a colorless oil.

후처리

  1. stirringthe mixture was stirred at the same temperature for 30 min
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1)

출처 및 근거

ORD 기록
ord-d975f3978eb0414f83e3b84337233733
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

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