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

HRID 14197

反応式

HRID 14197 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒2 回

反応条件

温度
80 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-20e5585ebb224339ae4db3c764c1d80e
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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