Butylamine → Methyl 3-bromo-5-(butylamino)-4-methoxybenzoate

HRID 14191

반응식

HRID 14191 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].Br[C:59]1[CH:60]=[C:61]([CH:66]=[C:67]([Br:71])[C:68]=1[O:69][CH3:70])[C:62]([O:64][CH3:65])=[O:63]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:71][C:67]1[CH:66]=[C:61]([CH:60]=[C:59]([NH:57][CH2:53][CH2:54][CH2:55][CH3:56])[C:68]=1[O:69][CH3:70])[C:62]([O:64][CH3:65])=[O:63]

참가 물질

7

반응물 4

HCID 8007ButylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 21086155Methyl 3,5-dibromo-4-methoxybenzoate

생성물 1

HCID 21086160Methyl 3-bromo-5-(butylamino)-4-methoxybenzoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매2회

반응 조건

온도
80 °C

실험 절차

To a stirred solution of Pd(OAc)2 (144 mg), BINAP (1.2 g), and cesium carbonate (8.4 g) in toluene (100 mL) was added butylamine (1.6 mL), and the mixture was heated at 80° C. for 15 min. A solution methyl 3,5-dibromo-4-methoxybenzoate (4.2 g) in toluene (30 mL) was added dropwise over 20 min. The mixture was refluxed overnight. The mixture was cooled to room temperature, filtered through diatomaceous earth, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes) provided 3.5 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.52, 7.19, 3.90, 3.88, 3.18, 1.66, 1.46, 0.97.

후처리

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through diatomaceous earth
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-cb35870106e04ff18d5775ee15a2958c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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