Sodium hydride → HCID 69092174, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxazole-4-carbohydrazide (228 mg, 1.794 mmol) in ethanol (8.9 mL) was added picolinimidamide hydrochloride (283 mg, 1.79 mmol). After heating the orange solution at 100° C. for 50 h, the solvent was removed in vacuo and the residue was azeotroped with toluene (2×4 mL) to give 514 mg of crude material. 187 mg of the crude material (0.75 mmol) was dissolved in N,N-dimethylformamide (3.7 mL) and treated with sodium hydride (60% dispersion in mineral oil, 75 mg, 1.9 mmol) in a single portion at ambient temperature. After stirring for 20 min, 1-(bromomethyl)-2-fluorobenzene (0.136 mL, 1.12 mmol) was added. The solution was stirred for an additional 45 min, at which point the solution was poured into water (75 mL) and extracted with ethyl acetate (3×50 mL). The organics were combined, washed with water (2×50 mL) and brine (1×50 mL), dried over magnesium sulfate, filtered, and the solvent was removed in vacuo to give the crude product as an orange oil. Purification by silica gel chromatography (10-100% ethyl acetate in hexanes) provided 4-(1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)oxazole, I-12 (58 mg, 0.18 mmol, 24% yield over two steps) as a tan solid and 4-(1-(2-fluorobenzyl)-5-(pyridin-2-yl)-1H-1,2,4-triazol-3-yl)oxazole, I-13 (21 mg, 0.06 mmol, 8.7% yield over two steps) as a brown solid.

Provenance & Evidence