Hydrochloric Acid → (S)-(6-bromo-2-methyl-3,4-dihydroquinoxalin-1 (2H)-yl)(cyclopropyl)methanone

HRID 1485672노트

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HRID 1485672 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]([C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[C@@H:7]([CH3:19])[CH2:8][N:9]2C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.C(O)C.Cl>O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[CH:4][CH:3]=1)[N:6]([C:20]([CH:22]1[CH2:23][CH2:24]1)=[O:21])[C@@H:7]([CH3:19])[CH2:8][NH:9]2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 118080289(S)-tert-butyl 7-bromo-4-(cyclopropanecarbonyl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate

생성물 1

HCID 118079082(S)-(6-bromo-2-methyl-3,4-dihydroquinoxalin-1 (2H)-yl)(cyclopropyl)methanone수율 93.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

A 200-mL round bottomed flask fitted with a nitrogen inlet, magnetic stir bar, and condenser was charged with (S)-tert-butyl 7-bromo-4-(cyclopropanecarbonyl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (5.74 g, 14.52 mmol), ethanol (100 mL), water (25 mL), and 6 M hydrochloric acid solution (2.66 mL, 15.97 mmol). The reaction mixture was heated to 50° C. for 24 h and then cooled to room temperature. The ethanol was removed under reduced pressure, the residue was extracted into dichloromethane (100 mL), and the extract was concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel (eluting with 3:2 hexanes-ethyl acetate) to afford (S)-(6-bromo-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)(cyclopropyl)methanone (4.00 g, 93%) as an off-white solid. MS (ESI, pos. ion) m/z 295, 297 [M+1]+.

후처리

  1. customA 200-mL round bottomed flask fitted with a nitrogen inlet, magnetic stir bar, and condenser
  2. temperaturecooled to room temperature
  3. customThe ethanol was removed under reduced pressure
  4. extractionthe residue was extracted into dichloromethane (100 mL)
  5. concentrationthe extract was concentrated under reduced pressure
  6. customThe crude material was purified by column chromatography on silica gel (eluting with 3:2 hexanes-ethyl acetate)

출처 및 근거

ORD 기록
ord-93c051a16e5f49ac8b912683d74f4bfd
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422281B2

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