N-bromobutanimide → Ethyl 1-(4-amino-3-bromo-5-(cyclopropylmethoxy)phenyl)cyclobutanecarboxylate

HRID 1183676노트

반응식

HRID 1183676 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:17][CH2:18][CH:19]1[CH2:21][CH2:20]1.C1C(=O)N([Br:29])C(=O)C1>C(Cl)(Cl)Cl.O>[NH2:1][C:2]1[C:3]([O:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)=[CH:4][C:5]([C:8]2([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:6][C:7]=1[Br:29]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 57995499Ethyl 1-(4-amino-3-(cyclopropylmethoxy)phenyl)cyclobutanecarboxylate

생성물 1

HCID 57995521Ethyl 1-(4-amino-3-bromo-5-(cyclopropylmethoxy)phenyl)cyclobutanecarboxylate수율 52.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

실험 절차

To a stirred solution of ethyl 1-(4-amino-3-(cyclopropylmethoxy)phenyl)cyclobutanecarboxylate (2.4 g, 8.3 mmol) in dry CHCl3 (50 mL), NBS (1.4 g, 7.8 mmol) was added at 0° C. The reaction mixture was allowed to stir for 3 h at room temperature. The reaction mixture was diluted with water, extracted with DCM (2×50 mL), the combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude reaction mixture was purified by column chromatography to yield ethyl 1-(4-amino-3-bromo-5-(cyclopropylmethoxy)phenyl)cyclobutanecarboxylate (1.5 g) as a yellow solid.

후처리

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialthe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude reaction mixture
  6. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-a1c561bd9668409b9c41b32252a3235e
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664249B2

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