M-Cresol → 4-Tert-butyl-2-{5-[(3-cyano-5-hydroxyindol-1-yl)methyl]benzofuran-2-yl}thiazole

HRID 1604669Notes

Reaction equation

HRID 1604669 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:12]1[N:13]=[C:14]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4[C:35]5[C:30](=[CH:31][C:32]([O:36]CC6C=CC=CC=6)=[CH:33][CH:34]=5)[C:29]([C:44]#[N:45])=[CH:28]4)=[CH:22][C:20]=3[CH:21]=2)[S:15][CH:16]=1)([CH3:11])([CH3:10])[CH3:9].C1C(O)=CC=CC=1C.C1(SC)C=CC=CC=1.C(S)(S)C.C(=O)([O-])O.[Na+]>O>[C:8]([C:12]1[N:13]=[C:14]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4[C:35]5[C:30](=[CH:31][C:32]([OH:36])=[CH:33][CH:34]=5)[C:29]([C:44]#[N:45])=[CH:28]4)=[CH:22][C:20]=3[CH:21]=2)[S:15][CH:16]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

8

Reactant 6

HCID 342M-CresolHCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 336451,1-EthanedithiolHCID 516892Sodium BicarbonateHCID 196038144-Tert-butyl-2-{5-[(3-cyano-5-benzyloxyindol-1-yl)methyl]benzofuran-2-yl}thiazole

Product 1

HCID 196037114-Tert-butyl-2-{5-[(3-cyano-5-hydroxyindol-1-yl)methyl]benzofuran-2-yl}thiazoleYield 68.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoroacetic acid (10 ml) was added to a mixture of 4-tert-butyl-2-{5-[(3-cyano-5-benzyloxyindol-1-yl)methyl]benzofuran-2-yl}thiazole (0.54 g), m-cresol (0.28 ml), thioanisole (0.28 ml) and ethanedithiol (0.56 ml) under ice-cooling. After being stirred for 4 hours, the mixture was poured into water (100 ml) and the resulting mixture was neutralized with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water, brine successively, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-{5-[(3-cyano-5-hydroxyindol-1-yl)methyl]benzofuran-2-yl}thiazole (305 mg).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine successively
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with a mixture of toluene and ethyl acetate
  7. additionThe fractions containing the objective compound
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2560cfad9ec64717bc29acd5152c3125
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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