Dimethylformamide → 3-Morpholinoquinoxaline-6-carbaldehyde

HRID 929346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929346
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:9]2)=[CH:4][CH:3]=1.[SiH](CC)(CC)CC.CN([CH:28]=[O:29])C>>[O:15]1[CH2:16][CH2:17][N:12]([C:8]2[CH:7]=[N:6][C:5]3[C:10]([N:9]=2)=[CH:11][C:2]([CH:28]=[O:29])=[CH:3][CH:4]=3)[CH2:13][CH2:14]1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 12052TriethylsilaneHCID 533635264-(7-Bromoquinoxalin-2-yl)morpholine

Produkt 1

HCID 866771723-Morpholinoquinoxaline-6-carbaldehydeAusbeute 82,3 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4-(7-bromoquinoxalin-2-yl)morpholine (59 g, 0.2 mol, 1.0 eq.) in DMF (500 mL) was added TEA (139 mL, 1.0 mol, 5.0 eq.), Et3SiH (127 mL, 0.8 mol, 4.0 eq) and Pd(dppf)Cl2CH2Cl2 (8.16 g, 0.01 mol, 0.05 eq.). The resulting mixture was stirred at 90° C. for 12 h in an autoclave under CO (1 MPa), then cooled and concentrated. The resulting residue was purified by flash column chromatography (EA/PE=1/1) to afford 3-morpholinoquinoxaline-6-carbaldehyde as a yellow solid (40 g, 82.3%).

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe resulting residue was purified by flash column chromatography (EA/PE=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-d3f9f73119b04233ba77312fd2f6788f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09295671B2

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