HCID 67228991, Verbindung → 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

HRID 1515686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515686
[CH:1]1([CH:6]=[C:7]([C:18]2[NH:29][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][O:27][CH3:28])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:29][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][O:27][CH3:28])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 1

HCID 67228991HCID 67228991, Verbindung

Produkt 1

HCID 532510852-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridineAusbeute 19,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (411 mg, 1.09) and 10% palladium on activated carbon (100 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 6 h. The mixture was cooled to room temperature before The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo and purified using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (80 mg, 19.4%) as a white solid: LC/MS m/e calcd for C23H28N2O3S [M+H]+ 413.56, observed 413.1; 1H NMR (400 MHz, CD3OD) δ ppm 8.30 (s, 1H), 8.20 (s, 1H), 7.89-7.93 (m, J=8.3 Hz, 2H), 7.55-7.66 (m, 2H), 6.67 (s, 1H), 4.61 (s, 2H), 4.37 (t, J=8.0 Hz, 1H), 3.33-3.48 (m, 3H), 3.08-3.13 (m, 3H), 2.25-2.33 (m, 1H), 2.12-2.20 (m, 1H), 1.61-1.88 (m, 5H), 1.45-1.56 (m, 2H), 1.18-1.31 (m, 2H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature before The catalyst
  2. customwas removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-b3ea1737d637441ba7aa08a200207cc1
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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