18-Crown-6 → HCID 59146121, 화합물

HRID 1512772노트

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HRID 1512772 반응식
FC(F)(F)COP([CH2:13][C:14]([O:16][CH3:17])=[O:15])(OCC(F)(F)F)=O.C1OCCOCCOCCOCCOCCOC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:48][C:49]1[CH:50]=[C:51]([C:59]2[O:63][N:62]=[C:61]([C:64]3[CH:65]=[CH:66][CH:67]=[C:68]4[C:72]=3[N:71]([CH3:73])[CH:70]=[C:69]4[CH:74]=O)[N:60]=2)[CH:52]=[CH:53][C:54]=1[O:55][CH:56]([CH3:58])[CH3:57]>C1COCC1>[Cl:48][C:49]1[CH:50]=[C:51]([C:59]2[O:63][N:62]=[C:61]([C:64]3[CH:65]=[CH:66][CH:67]=[C:68]4[C:72]=3[N:71]([CH3:73])[CH:70]=[C:69]4/[CH:74]=[CH:13]\[C:14]([O:16][CH3:17])=[O:15])[N:60]=2)[CH:52]=[CH:53][C:54]=1[O:55][CH:56]([CH3:57])[CH3:58]

참가 물질

6

반응물 4

HCID 2855718-Crown-6HCID 184894Nsc 634137HCID 2724254Sodium bis(trimethylsilyl)amideHCID 591461277-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde

생성물 1

HCID 59146121HCID 59146121, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-70 °C

실험 절차

To a solution of methyl {bis[(2,2,2-trifluoroethyl)oxy]phosphoryl}acetate (0.16 mL), 18-crown-6 (1.0 g) in THF (5 mL) stirred under nitrogen at −70° C. was added NaHMDS (1.0 mol/L in THF, 0.8 mL) during 1 min. The reaction mixture was stirred at −70° C. for 10 mins. 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde (200 mg) was added and the mixture was stirred at this temperature for 1.5 h and then left to warm to room temperature overnight. The reaction mixture was quenched with saturated ammonium chloride solution, diluted with water (25 mL) and extracted with ethyl acetate (50 mL). The organic phase was washed with brine, dried over sodium sulphate and evaporated to afford the crude product, which was purified by column chromatography (10% ethyl acetate in hexane) to afford methyl (2Z)-3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]-2-propenoate (D63) (120 mg). MS (ES): C24H22ClN3O4 requires 451; found 452.2 (M+H+).

후처리

  1. stirringthe mixture was stirred at this temperature for 1.5 h
  2. waitleft
  3. temperatureto warm to room temperature overnight
  4. customThe reaction mixture was quenched with saturated ammonium chloride solution
  5. additiondiluted with water (25 mL)
  6. extractionextracted with ethyl acetate (50 mL)
  7. washThe organic phase was washed with brine
  8. dry with materialdried over sodium sulphate
  9. customevaporated
  10. customto afford the crude product, which
  11. customwas purified by column chromatography (10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-ac4df8f94ad840768c83ecb375c9422b
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217028B2

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