Pyridine → Ethyl 3-{[(benzyloxy)carbonyl]amino}-7-bromo-6-fluoroquinoline-2-carboxylate

HRID 924380노트

반응식

HRID 924380 반응식
[NH2:1][C:2]1[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([F:12])=[C:7]([Br:13])[CH:6]=2.N1C=CC=CC=1.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>C(Cl)Cl.CCOC(C)=O>[CH2:29]([O:28][C:26]([NH:1][C:2]1[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([F:12])=[C:7]([Br:13])[CH:6]=2)=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 86726863Ethyl 3-amino-7-bromo-6-fluoroquinoline-2-carboxylate

생성물 1

HCID 86726865Ethyl 3-{[(benzyloxy)carbonyl]amino}-7-bromo-6-fluoroquinoline-2-carboxylate수율 68%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-10 °C

실험 절차

DCM (10.0 mL) was added to a mixture of ethyl 3-amino-7-bromo-6-fluoroquinoline-2-carboxylate (882.5 mg, 2.818 mmol) and pyridine (592.1 mg, 7.485 mmol). The mixture was cooled to −10° C. A solution of benzyl chloroformate (650.6 mg, 3.623 mmol) in DCM (5.0 mL) was added slowly over a period of 5 min. The mixture was then allowed to warm to room temperature and was stirred for 2 h. The reaction mixture was diluted with EtOAc (100 mL), washed with saturated aq. NaHCO3 (100 mL) and brine (100 mL), then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (0-30% EtOAc in hexanes) to give the sub-title compound as an off-white solid (854.9, 68%). LCMS calc. for C20H17BrFN2O4 (M+H)+: m/z=447.0. found 447.0.

후처리

  1. temperatureto warm to room temperature
  2. washwashed with saturated aq. NaHCO3 (100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by flash chromatography on silica gel (0-30% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-aff41ac08d8a4fd8becb9481a10986d5
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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