تفاعل #85435

معادلة التفاعل

compound 145-H

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

→

compound 146-A

المردود 57.0%

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

المردود 57.0%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   ترشيحthe catalyst was filtered
2. 2
   ترشيحThe reaction was filtered
3. 3
   workup.STIRRINGshaken at 20 psi H2 for an additional 24 h
4. 4
   ترشيحThe reaction mixture was filtered
5. 5
   أخرىevaporated
6. 6
   أخرىthe free base isolated
7. 7
   غسيلby washing with aqueous sodium bicarbonate
8. 8
   أخرىThe resultant residue was purified by flash column chromatography (SiO2)
9. 9
   غسيلeluting with 3% MeOH/CH2Cl2

الإجراء التجريبي

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+).

المصدر