18-Crown-6 → HCID 59146121、化合物

HRID 1512772ノート

反応式

HRID 1512772 の反応式
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]

参加物

6

反応物 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

生成物 1

HCID 59146121HCID 59146121、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-ac4df8f94ad840768c83ecb375c9422b
出典データセット
uspto-grants-2012_07
特許番号
US08217028B2

反応ノート

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