Reaktion #2287948

Reaktionsgleichung

4-bromo-6-morpholinobenzo[c][1,2,5]oxadiazole

compound 1012

4-bromo-6-morpholinobenzo[c][1,2,5]oxadiazole

(cis)-N1-(pyrimidin-2-yl)cyclohexane-1,4-diamine hydrochloride

cesium carbonate

→

(cis)-N1-(6-morpholinobenzo[c][1,2,5]oxadiazol-4-yl)-N4-(pyrimidin-2-yl)cyclohexane-1,4-diamine

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas flushed with nitrogen gas
2. 2
   FiltrationThe mixture was filtered though a layer of diatomaceous earth
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   Sonstigepurified by medium pressure silica gel chromatography (0 to 80% EtOAc/hexanes gradient)

Vorschrift

As shown in step 5-iii of Scheme 5, a mixture of 4-bromo-6-morpholinobenzo[c][1,2,5]oxadiazole (compound 1012, 147 mg, 0.5 mmol), (cis)-N1-(pyrimidin-2-yl)cyclohexane-1,4-diamine hydrochloride (120 mg, 0.6 mmol), (rac)-BINAP (32 mg, 0.05 mmol), Pd2(dba)3 (24 mg, 0.026 mmol), and cesium carbonate (506 mg, 1.55 mmol) in toluene (5 mL) was flushed with nitrogen gas and stirred overnight at 90° C. under an atmosphere of nitrogen. The mixture was filtered though a layer of diatomaceous earth, concentrated under reduced pressure, and purified by medium pressure silica gel chromatography (0 to 80% EtOAc/hexanes gradient) to provide (cis)-N1-(6-morpholinobenzo[c][1,2,5]oxadiazol-4-yl)-N4-(pyrimidin-2-yl)cyclohexane-1,4-diamine (compound 23) as an orange solid: 1H-NMR (300 MHz, CDCl3) δ 8.20 (d, J=4.9 Hz, 2H), 6.46 (t, J=4.8 Hz, 1H), 6.05 (d, J=1.6 Hz, 1H), 5.82 (s, 1H), 5.24 (s, 1H), 4.82 (d, J=7.0 Hz, 1H), 3.98 (s, 1H), 3.85-3.72 (m, 4H), 3.60 (s, 1H), 3.23-3.06 (m, 4H), 1.95-1.62 (m, 8H).

Quelle