تفاعل #10324

معادلة التفاعل

1-[(2,5-dibromothieno[2.3-b]thien-3-yl)methyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine

1-[(2,5-Dibromothieno[2.3-b]thien-3-yl)methyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine

hydrogen

→

title compound

المردود 9.4%

3-{[(4-Fluorophenyl)sulfonyl]methyl}1-(thieno[2.3-b]thien-3-ylmethyl)azetidine

المردود 9.4%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe catalyst was removed by filtration through Celite®
2. 2
   غسيلwashing with methanol
3. 3
   workup.ADDITIONafter the addition of triethylamine (30 μL)
4. 4
   أخرىto quench any HBr
5. 5
   أخرىformed
6. 6
   تركيزThe filtrate was concentrated in vacuo
7. 7
   أخرىThe residue was purified by preparative TLC (50% ethyl acetate/isohexane)

الإجراء التجريبي

A mixture of 1-[(2,5-dibromothieno[2.3-b]thien-3-yl)methyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine (Step 4, 39 mg, 0.07 mmol) and 10% palladium on carbon (50 mg) in methanol (7 mL) was stirred under a balloon of hydrogen for 3.5 hours. The catalyst was removed by filtration through Celite®, washing with methanol after the addition of triethylamine (30 μL) to quench any HBr formed. The filtrate was concentrated in vacuo. The residue was purified by preparative TLC (50% ethyl acetate/isohexane) to give the title compound (2.5 mg). 1H NMR (500 MHz, CDCl3) δ 7.91–7.89 (2H, m), 7.34 (1H, dd, J=1.0, 5.2 Hz), 7.23 (3H, t, J=7.3 Hz), 7.10 (1H, s), 3.70 (2H, s), 3.47 (2H, t, J=7.3 Hz), 3.38 (2H, d, J=7.3 Hz), 2.96 (2H, br s), 2.88–2.82 (1H, m).

المصدر