Ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate → Ethyl 3-(cyclopropylmethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate

HRID 1006275

Reaktionsgleichung

Reaktionsgleichung von HRID 1006275
[C:1]1(=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[C:6]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:3][CH2:2]1.[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(O)C>[CH:1]1([CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=3)[C:6]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 22676741Ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22676804Ethyl 3-(cyclopropylmethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131709914Lindlars catalystKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate (Example 182, 140 mg, 0.351 mmol) was stirred over Lindlar catalyst (28 mg) in ethanol (15 mL) under 1 atmosphere of hydrogen for 1 hour. The mixture was filtered through Celite with an excess of ethanol. The filtrate was concentrated, and the resulting crude oil was purified by flash chromatography on silica gel eluted with 20% Et2O/hexane. The title compound was collected as a yellow oil (95 mg, 67%). The product had: 1H NMR (300 MHz, acetone-d6) δ 7.78 (d, 1 H), 7.56-7.45 (m, 4 H), 7.34-7.32 (m, 1 H), 7.28-7.26 (m, 1 H), 7.16-7.13 (m, 1 H), 5.93 (s, 2 H), 4.32 (q, 2 H), 3.08 (d, 2 H), 1.31 (t, 3 H), 1.13-1.15 (m, 1 H), 0.42-0.38 (m, 2 H), 0.29-0.26 (m, 2 H).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite with an excess of ethanol
  2. concentrationThe filtrate was concentrated
  3. customthe resulting crude oil was purified by flash chromatography on silica gel
  4. washeluted with 20% Et2O/hexane
  5. customThe title compound was collected as a yellow oil (95 mg, 67%)

Quellen und Nachweise

ORD-Eintrag
ord-2dd0859076c34bb08df8cfd364fcd101
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787651B2

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