Nitrogen → HCID 10736491, compound

Participants

Reaction Conditions

Reaction Steps

This acetylene (7.6 g, 25 mmol), 2-iodo-4-(1,2,4-triazol-4-yl)aniline (5.6 g, 19.6 mmol), LiCl (927 mg, 19.7 mmol), Na2CO3 (8.37 g, 79 mmol), and Ph3P (1.03 g, 3.93 mmol) were stirred in DMF (200 ml) at r.t. for 2 h whilst N2 gas was bubbled through the mixture. Pd(OAc)2 (441 mg, 1.97 mmol) was then added, and the reaction heated at 100° C. for 20 h. The mixture was cooled, filtered and evaporated. H2O (500 ml) was added, and extracted with ethyl acetate (×5). The combined organic layers were washed with H2O, brine, dried, and evaporated. A mixture of EtOH and 5M HCl (300 ml, 1:1 v/v) was added, and the solution stood at r.t. for 18 h, then poured into saturated K2CO3, and extracted with EtOAc (×3). The organic layers were washed with water and brine, dried, evaporated, and purified by flash chromatography, eluting with CH2Cl2 :MeOH (92:8 v/v) to give (R)-3-(3-benzyloxy-2-hydroxyprop-1-yl)-5-(1,2,4-triazol-4-yl)indole (1.81 g, 26%).

Provenance & Evidence