Morpholine → (8-fluoro-4H-thieno[3,2-c]chromen-2-yl)(morpholino)methanone

HRID 84715

Reaktionsgleichung

Reaktionsgleichung von HRID 84715
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl-].C[Al+]C.[F:11][C:12]1[CH:21]=[CH:20][C:19]2[O:18][CH2:17][C:16]3[CH:22]=[C:23]([C:25]([O-])=[O:26])[S:24][C:15]=3[C:14]=2[CH:13]=1>ClCCCl>[F:11][C:12]1[CH:21]=[CH:20][C:19]2[O:18][CH2:17][C:16]3[CH:22]=[C:23]([C:25]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:26])[S:24][C:15]=3[C:14]=2[CH:13]=1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 16686359Dimethylalumanylium chlorideHCID 212791038-fluoro-4H-thieno[3,2-c]chromene-2-carboxylate

Produkt 1

HCID 57900498(8-fluoro-4H-thieno[3,2-c]chromen-2-yl)(morpholino)methanoneAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a cooled solution (ice/H2O) of morpholine in DCE was added slowly dropwise 2 equiv. of dimethylaluminum chloride. This reaction was stirred for greater than 30 minutes until reaching ambient temperature. Next the reaction was again cooled (ice/H2O) and 8-fluoro-4H-thieno[3,2-c]chromene-2-carboxylate was added as a solid portion wise. The reaction was allowed to equilibrate to ambient temp and monitored by LC/MS. The completed reaction was quenched with an aqueous solution of Na, K-tartrate (20% wt/wt). This mixture was extracted with EtOAc and the organic was washed with saline and dried (MgSO4). The dried org. was concentrated in vacuo to a residue. This residue was not soluble in DMF and 170bp as a white solid was collected by vacuum filtration, Yield=40% of theoretical. MS: (ESI+)=320.5

Aufarbeitung

  1. customuntil reaching ambient temperature
  2. additionwas added as a solid portion wise
  3. customto equilibrate to ambient temp
  4. customThe completed reaction
  5. customwas quenched with an aqueous solution of Na, K-tartrate (20% wt/wt)
  6. extractionThis mixture was extracted with EtOAc
  7. washthe organic was washed with saline
  8. dry with materialdried (MgSO4)
  9. concentrationwas concentrated in vacuo to a residue
  10. filtrationwas collected by vacuum filtration, Yield=40% of theoretical

Quellen und Nachweise

ORD-Eintrag
ord-72aca590b4f548b4a3bc4f90491ea9e2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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