1-Azabicyclo[3.2.2]nonan-4-one → 7-bromo-9-fluoro-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 37800

반응식

HRID 37800 반응식
Cl.[Br:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[NH:10]N.[N:12]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[C:15](=O)[CH2:14][CH2:13]2>Cl.C(O)(=O)C>[Br:2][C:3]1[C:4]2[NH:10][C:15]3[CH:16]4[CH2:19][CH2:20][N:12]([CH2:13][C:14]=3[C:5]=2[CH:6]=[C:7]([F:9])[CH:8]=1)[CH2:18][CH2:17]4

참가 물질

4

반응물 2

HCID 64203071-Azabicyclo[3.2.2]nonan-4-oneHCID 16370085(2-Bromo-4-fluorophenyl)hydrazine hydrochloride

생성물 1

HCID 672399477-bromo-9-fluoro-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

시약·촉매·용매 1

HCID 22641269Acetate-hydrochloric acid용매

반응 조건

온도
80 °C

실험 절차

(2-Bromo-4-fluorophenyl)hydrazine hydrochloride (1.14 g, 4.72 mmol; Enamine) was suspended in HCl-acetic acid (1.0 M, 25 mL; Aldrich). The product of Example 1A (684 mg, 4.91 mmol) was added and the reaction was heated to 80° C. for 5 hours. The reaction was then allowed to cool and then concentrated. The product was triturated with acetonitrile and isolated by filtration, washing with additional acetonitrile (2×10 mL). The solid was partitioned between 1.0 M NaOH (50 mL) and CHCl3 (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.05-2.11 (m, 4H), 3.01-3.14 (m, 3H), 3.19-3.26 (m, 2H), 4.17 (s, 2H), 6.96-7.04 (m, 2H); MS (DCI/NH3) m/z 309/311 (M+H)+. Anal. Calcd. for C14H14BrFN2: C, 54.39; H, 4.56; N, 9.06. Found: C, 54.04; H, 4.28; N, 8.90.

후처리

  1. temperatureto cool
  2. concentrationconcentrated
  3. customThe product was triturated with acetonitrile
  4. customisolated by filtration
  5. washwashing with additional acetonitrile (2×10 mL)
  6. customThe solid was partitioned between 1.0 M NaOH (50 mL) and CHCl3 (3×50 mL)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d1294aa47dad4b06977bd4955b3678ba
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524703B2

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