Butylamine → Methyl 3-(butylamino)-4-nitrobenzoate

HRID 348987

반응식

HRID 348987 반응식
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:53]([NH2:57])[CH2:54][CH2:55][CH3:56].[N+:58]([C:61]1[CH:70]=[CH:69][C:64]([C:65]([O:67][CH3:68])=[O:66])=[CH:63][C:62]=1OS(C(F)(F)F)(=O)=O)([O-:60])=[O:59]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:53]([NH:57][C:70]1[CH:69]=[C:64]([CH:63]=[CH:62][C:61]=1[N+:58]([O-:60])=[O:59])[C:65]([O:67][CH3:68])=[O:66])[CH2:54][CH2:55][CH3:56]

참가 물질

7

반응물 4

HCID 8007ButylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 54135622Methyl 4-nitro-3-{[(trifluoromethyl)sulfonyl]oxy}benzoate

생성물 1

HCID 21086162Methyl 3-(butylamino)-4-nitrobenzoate

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매2회

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온도
80 °C

실험 절차

To a stirred solution of Pd2(dba)3 (139 mg), BINAP (284 mg), and cesium carbonate (2.0 g) in toluene (50 mL) was added butylamine (0.45 mL), and the reaction mixture was heated at 80° C. for 15 min. A solution of methyl 4-nitro-3-{[(trifluoromethyl)sulfonyl]oxy}benzoate (1.0 g) in toluene (15 mL) was added dropwise over 1 h. The mixture was cooled to room temperature, filtered through diatomaceous earth, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 3:1 ethyl acetate/hexanes) provided 670 mg of the title compound as a yellow oil: ESI MS m/z 550 [M+H]+.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash column chromatography (silica, 3:1 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-9f481d5ab09143dfbbf004fdee9dfbfb
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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