Reaktion #677172

Reaktionsgleichung

tert-butyl 3-(methylsulfonyl)-4-oxo-1-(1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridine-5(4H)-carboxylate

cyclopentanethiol

NaH

→

title compound

3-(Cyclopentylsulfanyl)-1-(1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridin-4(5H)-one

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with aqueous NH4Cl
2. 2
   Extraktionextracted with CH2Cl2
3. 3
   TrocknenThe combined extracts were dried (Na2SO4)
4. 4
   Einengenconcentrated
5. 5
   SonstigePurification
6. 6
   Waschenby silica gel chromatography (gradient elution, 0-100% EtOAc /hexanes)

Vorschrift

To a solution of cyclopentanethiol (54 μL, 0.50 mmol) in THF (0.5 mL) at 0° C. was added NaH (20.0 mg, 0.50 mmol). The reaction mixture was warmed to rt and tert-butyl 3-(methylsulfonyl)-4-oxo-1-(1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridine-5(4H)-carboxylate (100 mg, 0.25 mmol) was added, After 30 min, the reaction was quenched with aqueous NH4Cl and extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and concentrated. Purification by silica gel chromatography (gradient elution, 0-100% EtOAc /hexanes) afforded the title compound. 1H NMR (400 MHz, ppm, CD3OD) δ 7.73 (d, J=2.3 Hz, 1 H); 6.50 (d, J=2.4 Hz, 1 H); 3.77 (m, 1 H); 3.44 (t, J=6.2 Hz, 2 H); 3.04 (t, J=6.3 Hz, 2 H); 2.32-2.22 (m, 2 H); 1.85-1.77 (m, 2 H); 1.76-1.65 (m, 4 H). HRMS (ES+) m/z 320.0879 [(M+H)+; calcd for C15 H17N3OS2: 320.0886].

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