18-Crown-6 → HCID 59146121, compound

HRID 1512772Notes

Reaction equation

HRID 1512772 reaction equation
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]

Participants

6

Reactant 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

Product 1

HCID 59146121HCID 59146121, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-ac4df8f94ad840768c83ecb375c9422b
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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