Trifluoroacetic acid → HCID 23589658, compound

HRID 1983489Notes

Reaction equation

HRID 1983489 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][O:18][C@H:19]4[CH2:23][CH2:22][O:21][CH2:20]4)[CH:15]=3)[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C([SiH](C(C)C)C(C)C)(C)C.FC(F)(F)C(O)=O.C(OCC)(=O)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][O:18][C@H:19]4[CH2:23][CH2:22][O:21][CH2:20]4)[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 138754Silane, tris(1-methylethyl)-HCID 23589659HCID 23589659, compound

Product 1

HCID 23589658HCID 23589658, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 82 mg of 3-(3-fluorophenyl)-5-{[(3S)tetrahydro-3-furanyloxy]methyl}-1-trityl-1H-indazole in 1.6 ml methylene chloride were added 0.05 ml of triisopropylsilane and 0.4 ml of trifluoroacetic acid, and the mixture was stirred at room temperature for 20 minutes. To the reaction mixture was added ethyl acetate. The mixture was sequentially washed with saturated aqueous sodium hydrogencarbonate solution (×2) and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. Then, the resulting crude product was purified and separated by silica gel column chromatography (ethyl acetate:toluene=1:4), to give 36 mg of the title compound as a viscous colorless oil.

Workup

  1. washThe mixture was sequentially washed with saturated aqueous sodium hydrogencarbonate solution (×2) and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThen, the resulting crude product was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:toluene=1:4)

Sources & evidence

ORD record
ord-57fbf49b7b7c43639088697a878a003b
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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