Reacción #169

ord-2d4104aef43247ff855d465ce3910528

Ecuación de reacción

O=C(NC1CCCCC1)c1ccc(Cl)nc1
O=C(NC1CCCCC1)c1ccc(
N#Cc1ccc(N)cc1
N#Cc1ccc(N)cc1
N#Cc1ccc(Nc2ccc(C(=O)NC3CCCCC3)cn2)cc1
N#Cc1ccc(Nc2ccc(C(=O
Rendimiento 9.9%

Disolventes

Condiciones de reacción

Temperatura
100°CELSIUS

Procedimiento

In a 50 mL round-bottomed flask a TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.115 g, 0.13 mmol),POTASSIUM TERT-BUTOXIDE (0.282 g, 2.51 mmol)and BINAP (0.157 g, 0.25 mmol) in dry 1,4-dioxane (10 mL) was mixed under N2.Followed by 6-chloro-N-cyclohexylnicotinamide (.300 g, 1.26 mmol) and 4-aminobenzonitrile (0.178 g, 1.51 mmol) was added and resulting mixture(dark brown) was heated at 100oC for 3 hrs.LCMS analysis showed the formation of required product.Reaction stopped,crude was passed through celite and washed with dioxane and finally with methanol.The filtrate was dried and dissolved in 3 ml DMSO for Waters MS Purification system.Pure fractions collected and concentrated.A White solid obtained as a product 6-(4-cyanophenylamino)-N-cyclohexylnicotinamide (0.040 g, 9.93 %).32 mg of above product was submitted for MGyrx2 projetct.LCMS/NMR confirmed the product.

Fuente

750 AstraZeneca ELN dataset