Réaction #1113994

Équation de réaction

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

Rendement 44.0%

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

Rendement 44.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

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

Mode opératoire

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

Source