Reaktion #805765

Reaktionsgleichung

compound 5f

tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoate

K2CO3

dimethyl (1-diazo-2-oxopropyl)phosphonate

→

compound 17a

tert-Butyl 4-(2-ethynyl-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoate

Lösungsmittel

DCM

MeOH

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated under reduced pressure
2. 2
   SonstigeThe residue obtained
3. 3
   Waschenwashed with water (20 mL)
4. 4
   ExtraktionThe aqueous layer was extracted with DCM (3×10 mL)
5. 5
   WaschenThe combined organic extracts were washed with brine
6. 6
   Trocknendried over MgSO4
7. 7
   FiltrationThe mixture was filtered
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto give a residue, which
10. 10
    Sonstigewas purified by flash column chromatography on silica gel (20-60% EtOAc/heptane)

Vorschrift

To a suspension of compound 5f (0.30 g, 0.73 mmol, Example 5) in MeOH (5 mL) was added K2CO3 (0.30 g, 2.2 mmol) and a solution of dimethyl (1-diazo-2-oxopropyl)phosphonate (0.18 g, 0.96 mmol) in MeOH (2 mL). The reaction mixture was stirred at rt for 2 days, and concentrated under reduced pressure. The residue obtained was dissolved in DCM (20 mL) and washed with water (20 mL). The aqueous layer was extracted with DCM (3×10 mL). The combined organic extracts were washed with brine, and dried over MgSO4. The mixture was filtered and concentrated to give a residue, which was purified by flash column chromatography on silica gel (20-60% EtOAc/heptane) to give the compound 17a as an off-white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C23H24N4O3: 405.2 (M+H). found: 405.2.

Quelle