Potassium Acetate → 2-Bromo-4-fluoro-6-(1-oxo-6,7,8,9-tetrahydropyrazino[1,2-a]indol-2(1H)-yl)benzaldehyde

HRID 519371

반응식

HRID 519371 반응식
[C:1]1(=[O:14])[C:6]2=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=3[N:5]2[CH:4]=[CH:3][NH:2]1.[Br:15][C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20](Br)[C:17]=1[CH:18]=[O:19].C([O-])(=O)C.[K+].COC1C2C(=C3C(=CC=2)C(OC)=CC=N3)N=CC=1>>[Br:15][C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([N:2]2[CH:3]=[CH:4][N:5]3[C:13]4[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=4[CH:7]=[C:6]3[C:1]2=[O:14])[C:17]=1[CH:18]=[O:19]

참가 물질

5

반응물 4

HCID 517044Potassium AcetateHCID 104622984,7-Dimethoxy-1,10-phenanthrolineHCID 444746662,6-Dibromo-4-fluorobenzaldehydeHCID 866837556,7,8,9-Tetrahydropyrazino[1,2-a]indol-1(2H)-one

생성물 1

HCID 866837562-Bromo-4-fluoro-6-(1-oxo-6,7,8,9-tetrahydropyrazino[1,2-a]indol-2(1H)-yl)benzaldehyde수율 49.3%

반응 조건

온도
100 °C

실험 절차

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 121e (500 mg, 2.66 mmol), 2,6-dibromo-4-fluorobenzaldehyde (1.50 g, 5.32 mmol), and potassium acetate (521 mg, 5.32 mmol). After bubbling argon through the suspension for 30 minutes, 4,7-dimethoxy-1,10-phenanthroline (638.4 mg, 2.66 mmol) and cuprous iodide (506 mg, 2.66 mmol) were added. The system was subjected to three cycles of vacuum/argon flush and then heated at 100° C. for 16 h. It was then cooled to room temperature and filtered. The solid was washed with dichloromethane (2×100 ml). The combined filtrate was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (10:1 to 3:1) to afford 121f (510 mg, 49%) as a yellow solid. MS: [M+H]+ 389.

후처리

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customAfter bubbling argon through the suspension for 30 minutes
  3. customflush
  4. temperatureIt was then cooled to room temperature
  5. filtrationfiltered
  6. washThe solid was washed with dichloromethane (2×100 ml)
  7. concentrationThe combined filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica-gel column chromatography
  9. washeluting with petroleum ether/ethyl acetate (10:1 to 3:1)

출처 및 근거

ORD 기록
ord-f77a60d2fa034cdb8b82d1d923a91ac0
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115152B2

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