Réaction #7787

Équation de réaction

5′-(1,3-benzoxazol-2-yl)-2′-(bromomethyl)-1,1′-biphenyl-3-carbonitrile

sodium cyanide

H2O

→

5′-(1,3-benzoxazol-2-yl)-2′-(cyanomethyl)-1,1′-biphenyl-3-carbonitrile

Solvants

DMF H2O

DMF

Conditions de réaction

Traitement

1. 1
   Extractionwas extracted with EtOAc (3×)
2. 2
   Lavagewashed with brine (2×)
3. 3
   Séchagedried over Na2SO4
4. 4
   Autreevaporated to dryness
5. 5
   Autreto give an orange oil
6. 6
   AutreThe crude was purified by flash chromatography on silica gel eluting with a gradient of EtOAc

Mode opératoire

A mixture of 5′-(1,3-benzoxazol-2-yl)-2′-(bromomethyl)-1,1′-biphenyl-3-carbonitrile (183 mg, 0.47 mmol) and sodium cyanide (46 mg, 0.94 mmol) in DMF:H2O (5:1, 18 mL) and DMF (20 mL) was stirred at rt for 3 h. H2O was added to the reaction mixture and it was extracted with EtOAc (3×). The organics were combined, washed with brine (2×), dried over Na2SO4, and evaporated to dryness to give an orange oil. The crude was purified by flash chromatography on silica gel eluting with a gradient of EtOAc:hexanes (0 to 30 min: 0 to 20% EtOAc) to afford the desired 5′-(1,3-benzoxazol-2-yl)-2′-(cyanomethyl)-1,1′-biphenyl-3-carbonitrile as a colorless solid (M.p. 175–176° C.). 1H NMR (CDCl3, 300 MHz) δ 8.34 (dd, 1H), 8.18 (s, 1H), 7.77 (m, 3H), 7.67 (m, 3H), 7.60 (m, 1H), 7.40 (m, 2H), 3.69 (s, 2H). MS (ESI) 336 (M+H)+.

Source