4-hydroxy-N-methylbenzamide

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl trifluoromethanesulfonate (200 μL, 1.76 mmol) was added to 4-hydroxy-N-methylbenzamide (6-A) (133 mg, 0.881 mmol) and the mixture stirred at 65° C. for 10 min. Toluene (0.6 mL) was added and the suspension stirred rapidly at 65° C. for 30 min. Toluene (0.4 mL), triethylamine (370 μL, 2.67 mmol) and a solution of 1-methyl-1H-indole-4-carbohydrazide (6-B) (100 mg, 0.528 mmol) in toluene (1.0 mL) and DMF (250 μL) were added and the mixture stirred at 65° C. for 3 h and then at 125° C. for 18 h. The mixture was evaporated in vacuo and the residue purified by preparative TLC (silica gel, methylene chloride:methanol, 95:5) to provide 4-[4-methyl-5-(1-methyl-1H-indol-4-yl)-4H-1,2,4-triazol-3-yl]phenol (6-C). 1H NMR (500 MHz, CD3OD): δ 3.63 (s, 3H); 3.92 (s, 3H); 6.53 (d, 1H); 7.00 (d, 2H); 7.37 (m, 3H); 7.64, (m, 3H). the suspension stirred rapidly at 65° C. for 30 min the mixture stirred at 65° C. for 3 h at 125° C. for 18 h The mixture was evaporated in vacuo the residue purified by preparative TLC (silica gel, methylene chloride:methanol, 95:5)