Reaktion #648586

Reaktionsgleichung

2-fluoro-4-(trifluoromethyl)benzaldehyde

Meldrum's acid

D,L-proline

compound

7-[(Methylsulfanyl)methyl]-1H-indole

→

title compound

Ethyl 3-[2-fluoro-4-(trifluoromethyl)phenyl]-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

Lösungsmittel

ethanol

pyridine

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenIt was concentrated
2. 2
   Sonstigeto result in 4.47 g of a crude product which
3. 3
   workup.ADDITIONwere added
4. 4
   TemperaturThe reaction mixture was heated
5. 5
   Temperaturunder reflux for 1 h
6. 6
   EinengenIt was concentrated
7. 7
   Sonstigethe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Vorschrift

1.54 g (8.00 mmol) of 2-fluoro-4-(trifluoromethyl)benzaldehyde, 1.15 g (8.00 mmol) of Meldrum's acid and 44 mg (0.38 mmol) of D,L-proline were added to a solution of 1.50 g (7.62 mmol) of the compound from Example 8A in 62 ml of acetonitrile. The reaction mixture was stirred at RT overnight. It was concentrated to result in 4.47 g of a crude product which was introduced into 48 ml of pyridine and 12 ml of ethanol, and 4 mg (63 μmol) of copper powder were added. The reaction mixture was heated under reflux for 1 h. It was concentrated, and the crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 2.74 g (82% of theory) of the title compound.

Quelle