Stannous chloride dihydrate → 4-(3-Bromopyridin-4-yloxy)-2,5-difluorobenzenamine

HRID 1046001노트

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HRID 1046001 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:10]=1[F:19].O.O.[Sn](Cl)Cl>CCO>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]([F:19])=[CH:11][C:12]([NH2:16])=[C:13]([F:15])[CH:14]=1

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 673986343-Bromo-4-(2,5-difluoro-4-nitrophenoxy)pyridine

생성물 1

HCID 673992554-(3-Bromopyridin-4-yloxy)-2,5-difluorobenzenamine수율 112%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

3-Bromo-4-(2,5-difluoro-4-nitrophenoxy)pyridine (0.414 g, 1.25 mmol) was dissolved in EtOH (30 mL). Tin (II) chloride dihydrate (1.129 g, 5.00 mmol) was added and the mixture was heated at 80° C. for 411. The solvent was removed under reduced pressure and the residue quenched with saturated aqueous NaHCO3. The mixture was diluted with EtOAc and filtered through Celite®. The Celite® bed was washed with water (2×) and EtOAc (2×), and the filtrate was extracted with EtOAc (2×). The combined organic extracts were dried and evaporated to yield 4-(3-bromopyridin-4-yloxy)-2,5-difluorobenzenamine (0.42 g, 112% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.68 (s, 1H), 8.33 (d, 1H), 7.28-7.23 (m, 1H), 6.76-6.71 (m, 2H), 5.56 (br s, 2H); MS (ESI) m/z: 301.0 (M+H+).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue quenched with saturated aqueous NaHCO3
  3. additionThe mixture was diluted with EtOAc
  4. filtrationfiltered through Celite®
  5. washThe Celite® bed was washed with water (2×) and EtOAc (2×)
  6. extractionthe filtrate was extracted with EtOAc (2×)
  7. customThe combined organic extracts were dried
  8. customevaporated

출처 및 근거

ORD 기록
ord-23c7f6b22e00435e81ebd02e742f34fe
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569319B2

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