Trifluoroacetic acid → 4-[3-(2-Methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester

HRID 1821515Notes

Reaction equation

HRID 1821515 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH:22]=O)=[CH:16][CH:15]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]=2[CH3:1])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 72242-MethylindoleHCID 12052TriethylsilaneHCID 10104031Methyl 4-(3-oxopropyl)benzoate

Product 1

HCID 670554944-[3-(2-Methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-Methyl-1H-indole (0.86 g, 5.2 mmol) and 4-(3-Oxo-propyl)-benzoic acid methyl ester (1.0 g, 5.2 mmol) in methylene chloride (50 mL), was added TFA (1.78 g, 15.6 mmol), followed by triethylsilane (1.81 g, 15.6 mmol). The reaction mixture was stirred overnight, quenched with sat. NaHCO3 solution (50 mL), and the organic layer was washed with sat. NaHCO3 solution, water, brine, and dried (Na2SO4). Solvent was removed under reduced pressure, and the residue was purified by flash column chromatography with 10-20% EtOAc/hexanes to yield the desired 4-[3-(2-Methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester in 88% (1.67 g) yield.

Workup

  1. customquenched with sat. NaHCO3 solution (50 mL)
  2. washthe organic layer was washed with sat. NaHCO3 solution, water, brine
  3. dry with materialdried (Na2SO4)
  4. customSolvent was removed under reduced pressure
  5. customthe residue was purified by flash column chromatography with 10-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-eb29a5813ef848d6aecb9de0ba0c8367
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

Loading…