Water → 5-(2'-Thioxospiro[cyclohexane-1,3'-[3H]indol]-5'-YL)-1-methyl-pyrrole-2-carbonitrile

HRID 276989

Reaktionsgleichung

Reaktionsgleichung von HRID 276989
O=[C:2]1[C:10]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:16]3[N:20]([CH3:21])[C:19]([C:22]#[N:23])=[CH:18][CH:17]=3)[CH:8]=2)[NH:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1.O>C1(C)C=CC=CC=1>[S:33]=[C:2]1[C:10]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:16]3[N:20]([CH3:21])[C:19]([C:22]#[N:23])=[CH:18][CH:17]=3)[CH:8]=2)[NH:3]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 219862515-(2'-oxospiro[cyclohexane-1,3'-[3H]indol]-5'-yl)-1-methyl-pyrrole-2-carbonitrile

Produkt 1

HCID 99271305-(2'-Thioxospiro[cyclohexane-1,3'-[3H]indol]-5'-YL)-1-methyl-pyrrole-2-carbonitrileAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5-(2′-oxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-1-methyl-pyrrole-2-carbonitrile (0.55 g, 1.8 mmol, 1 eq) in toluene (50 mL) was added Lawesson's reagent (0.47 g, 1.1 mmol, 0.65 eq) and the reaction was heated to 80° C. for 1 hour. The reaction was cooled to room temperature, poured into water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were combined, washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography on silica gel gave the product as a white solid (0.32 g, 55%). 1H NMR (d6-DMSO, 500 MHz) δ 1.36-1.99 (m, 10 H), 3.7(s,3 H),6.35 (d, 1 H, J=4.2 Hz), 7.05 (d, 1 H, J=4.2 Hz),7.16 (d, 1 H, J=7.9 Hz), 7.44 (dd, 1 H, J=1.6, 8.1 Hz), 7.83 (d, 1 H, J=1.6 Hz), 12.75 (s, 1 H). MS (ESI) [M−H]−=320. Anal. calcd. for C19H19N3S: C, 70.99; H, 5.96; N, 13.07. Found: C, 68.69; H, 5.36; N, 12.27.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9d1db2a9ec35494ab85267b8a8b66b24
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355648B1

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