Reaktion #85435

Reaktionsgleichung

compound 145-H

3-Bromo-thieno[3,2-b]pyridin-2-ylamine hydrochloride

→

compound 146-A

Ausbeute 57.0%

Thieno[3,2-b]pyridin-2-ylamine hydrochloride

Ausbeute 57.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe catalyst was filtered
2. 2
   FiltrationThe reaction was filtered
3. 3
   workup.STIRRINGshaken at 20 psi H2 for an additional 24 h
4. 4
   FiltrationThe reaction mixture was filtered
5. 5
   Sonstigeevaporated
6. 6
   Sonstigethe free base isolated
7. 7
   Waschenby washing with aqueous sodium bicarbonate
8. 8
   SonstigeThe resultant residue was purified by flash column chromatography (SiO2)
9. 9
   Wascheneluting with 3% MeOH/CH2Cl2

Vorschrift

A mixture of compound 145-H, (1.86 g, 6.16 mmol) and 10% Pd/C (0.49 g, 26.3% w/w) in methanol (75 mL) was catalytically hydrogenated on a Parr shaker at 25 psi. After 3 h, the catalyst was filtered, the reaction mixture recharged with 10% Pd/C (0.49 g, 26.3% w/w) and shaken an additional 16 h at 22 psi H2. The reaction was filtered, recharged with 10% Pd/C (0.20 g, 10.8% w/w), and shaken at 20 psi H2 for an additional 24 h. The reaction mixture was filtered, evaporated, and the free base isolated by washing with aqueous sodium bicarbonate. The resultant residue was purified by flash column chromatography (SiO2), eluting with 3% MeOH/CH2Cl2 to afford compound 146-A as a yellow solid (0.65 g, 57%). 1H-NMR (DMSO-d6): δ 6.4 (s, 1H), 7.1 (dd, 1H), 8.3 (2, 1H), 8.4 (s, 2H), 8.5 (d, 1H), 15.2 (br s, 1H); MS: m/z 151.1 (MH+).

Quelle