반응 #85435

반응 방정식

compound 145-H

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

→

compound 146-A

수율 57.0%

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

수율 57.0%

용매

methanol

반응 조건

후처리

1. 1
   여과the catalyst was filtered
2. 2
   여과The reaction was filtered
3. 3
   workup.STIRRINGshaken at 20 psi H2 for an additional 24 h
4. 4
   여과The reaction mixture was filtered
5. 5
   기타evaporated
6. 6
   기타the free base isolated
7. 7
   세척by washing with aqueous sodium bicarbonate
8. 8
   기타The resultant residue was purified by flash column chromatography (SiO2)
9. 9
   세척eluting with 3% MeOH/CH2Cl2

실험 절차

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+).

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