Reaktion #1967269

Reaktionsgleichung

DME

N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]oxazol-2-amine

2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

sodium carbonate anhydrous

→

N-(4-(3-(3,6-DIHYDRO-2H-PYRAN-4-YL)PYRIDIN-2-YLOXY)PHENYL)BENZO[D]OXAZOL-2-AMINE

Lösungsmittel

EtOH

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA glass microwave reaction vessel
2. 2
   Sonstigethe reaction mixture was sealed under argon
3. 3
   SonstigeThe reaction mixture was partitioned between EtOAc/water
4. 4
   Extraktionthe aqueous layer was extracted with EtOAc (3×)
5. 5
   SonstigeThe combined organic layers were evaporated onto silica gel
6. 6
   Sonstigepurified by flash chromatography (Isco (80 gram))
7. 7
   Wascheneluting with EtOAc:hexanes (0:1→1:2)
8. 8
   Sonstigeto give a light-orange amorphous solid

Vorschrift

A glass microwave reaction vessel was charged with N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]oxazol-2-amine (0.500 g, 1.308 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.414 g, 1.971 mmol), sodium carbonate anhydrous (0.700 g, 6.60 mmol) and trans-dichlorobis(triphenyl-phosphine)palladium (II) (0.092 g, 0.131 mmol, Strem). A mixture of 7:3:2 DME:H2O:EtOH (11 mL) was added and the reaction mixture was sealed under argon and heated in a Emrys Optmizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 140° C. for 15 min. The reaction mixture was partitioned between EtOAc/water and the aqueous layer was extracted with EtOAc (3×). The combined organic layers were evaporated onto silica gel and purified by flash chromatography (Isco (80 gram)) eluting with EtOAc:hexanes (0:1→1:2) to give a light-orange amorphous solid. MS (ESI, pos. ion) m/z: 386.0 (M+1). IC50 (uM) +++++.

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