Triethylamine → HCID 57791832, 화합물

HRID 1091776노트

반응식

HRID 1091776 반응식
[Br-].[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7](=[O:31])O[CH:9]2[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[F:32][C:33]1[CH:40]=[CH:39][C:38]([CH:41]=O)=[CH:37][C:34]=1[C:35]#[N:36].C(N(CC)CC)C.O.[NH2:51][NH2:52]>CN(C=O)C.CCO.O.C(OCC)(=O)C.C(Cl)Cl>[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7](=[O:31])[NH:51][N:52]=[C:9]2[CH2:41][C:38]2[CH:39]=[CH:40][C:33]([F:32])=[C:34]([CH:37]=2)[C:35]#[N:36])=[CH:5][CH:4]=1

참가 물질

10

반응물 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 27695822-Fluoro-5-formylbenzonitrileHCID 86633040(6-Bromo-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide

생성물 1

HCID 57791832HCID 57791832, 화합물수율 41.4%

시약·촉매·용매 5

HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

(6-bromo-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide (95) (9.0 g, 16.24 mmol) and 2-fluoro-5-formylbenzonitrile (2.91 g, 19.49 mmol) were dissolved DCM (60 mL), to this was added triethylamine (2.94 mL, 21.11 mmol) and the reaction was stirred overnight. The reaction mixture was quenched with water (50 mL), extracted with DCM (2×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford an orange gum. This was passed through a plug of silica eluting with ethyl acetate to afford a yellow gum. To this was added water (40 mL), EtOH (40 mL) and DMF (4 mL). Hydrazine hydrate (8.13 g, 162.39 mmol) was added and the reaction was heated at reflux overnight. The reaction was cooled and the precipitate was collected by filtration, washed with EtOH (25 mL) and air dried to afford the desired compound as a white solid (2.410 g, 41.4% yield), which was used without further purification; 1H NMR (400.132 MHz, DMSO) δ 4.38 (2H, s), 7.48 (1H, t), 7.75-7.71 (1H, m), 7.89 (1H, dd), 8.02 (1H, d), 8.18 (1H, d), 8.22 (1H, s), 12.64 (1H, s); m/z (LC-MS, ESI−), RT=2.18 (M−H 358).

후처리

  1. customThe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with DCM (2×75 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford an orange gum
  7. customto afford a yellow gum
  8. temperaturethe reaction was heated
  9. temperatureat reflux overnight
  10. temperatureThe reaction was cooled
  11. filtrationthe precipitate was collected by filtration
  12. washwashed with EtOH (25 mL) and air
  13. customdried

출처 및 근거

ORD 기록
ord-01df70d74ca548b6b2abffeb9a922eae
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129380B2

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