Reaktion #677171

Reaktionsgleichung

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

TFA

→

title compound

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

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting mixture was quenched with saturated aq. NaHCO3
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, 0-10% MeOH/dichloromethane)

Vorschrift

To a solution of tert-butyl 3-(methylsulfanyl)-4-oxo-1-(1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridine-5(4H)-carboxylate (20 mg, 0.055 mmol) in CH2Cl2 (274 μL) at 0° C. was added TFA (274 μL). The solution was stirred at 0° C. for 15 min. The resulting mixture was quenched with saturated aq. NaHCO3 and extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and concentrated. Purification by silica gel chromatography (gradient elution, 0-10% MeOH/dichloromethane) afforded the title compound. 1H NMR (400 MHz, ppm, CDCl3) δ 11.66 (s, 1 H); 8.05 (s, 1 H); 7.77 (d, J=2.6 Hz, 1 H); 6.53 (d, J=2.6 Hz, 1 H); 3.58 (t, J=6.5 Hz, 2 H); 3.07 (t, J=6.5 Hz, 2 H); 2.64 (s, 3 H). HRMS (ES+) m/z 266.0414 [(M+H)+; calcd for C11H11N3OS2: 266.0416].

Quelle