Reaktion #497151

Reaktionsgleichung

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

Ausbeute 44.0%

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

Ausbeute 44.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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

Quelle