반응 #497151

반응 방정식

sodium triacetoxyborohydride

325

6-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)nicotinaldehyde

amine

2-(2-methoxyethoxy)ethanamine

acetic acid

sodium triacetoxyborohydride

→

327

수율 44.0%

N-((6-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)-2-(2-methoxyethoxy)ethanamine

수율 44.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGstirred at r.t. for 16 h
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITcontinued for 2 h
4. 4
   기타The reaction mixture was partitioned between dichloromethane and 1N NaOH
5. 5
   기타The yellow suspension was removed by filtration
6. 6
   세척rinsed with dichloromethane and 1N NaOH
7. 7
   추출The organic extract
8. 8
   건조was dried over anhydrous sodium sulfate
9. 9
   여과filtered
10. 10
    농축concentrated
11. 11
    기타The residue was purified via Biotage (linear gradient 0-20%, methanol/dichloromethane; Snap 100 g column)

실험 절차

A suspension of carbaldehyde 325 (0.50 g, 1.3 mmol), amine 326 (0.30 g, 2.5 mmol) and acetic acid (0.14 ml, 2.5 mmol) in dichloromethane (20 ml) was stirred for 1 h at room temperature. Then sodium triacetoxyborohydride (0.80 g, 3.8 mmol) was added and stirred at r.t. for 16 h. A further amount of sodium triacetoxyborohydride (1.0 g) was then added, and stirring continued for 2 h. The reaction mixture was partitioned between dichloromethane and 1N NaOH. The yellow suspension was removed by filtration and rinsed with dichloromethane and 1N NaOH. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified via Biotage (linear gradient 0-20%, methanol/dichloromethane; Snap 100 g column) to yield 327 (280 mg, 0.562 mmol, 44%) as a yellow solid. LRMS (M+H): 499.4

출처