Potassium Carbonate → HCID 17822421, compound

HRID 1604665Notes

Reaction equation

HRID 1604665 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([OH:29])=[CH:26][CH:27]=5)[C:22]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:35](=[O:38])([O-])[O-:36].[K+].[K+]>CN(C)C=O>[CH2:14]([O:36][C:35]([CH2:2][CH2:1][CH2:3][O:29][C:25]1[CH:24]=[C:23]2[C:28](=[CH:27][CH:26]=1)[N:20]([CH2:19][C:16]1[CH:17]=[CH:18][C:12]3[O:11][C:10]([C:7]4[S:8][CH:9]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[N:6]=4)=[CH:14][C:13]=3[CH:15]=1)[CH:21]=[C:22]2[CH2:30][C:31]([O:33][CH3:34])=[O:32])=[O:38])[C:13]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:12]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 17928195HCID 17928195, compound

Product 1

HCID 17822421HCID 17822421, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-hydroxyindole-3-acetate (0.474 g), benzyl 4-bromobutylate (0.34 g) and potassium carbonate (0.19 g) in N,N-dimethylformamide (5 ml) was stirred at 50° C. for 8 hours. After being cooled to room temperature, the mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give methyl 5-[3-(benzyloxycarbonyl)propoxy]-1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}indole-3-acetate (0.36 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with a mixture of n-hexane and ethyl acetate
  7. additionThe fractions containing the objective compound
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f383f759c01a49fa8587845655ff130f
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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