Pivalaldehyde → HCID 57929939, compound

Participants

Reaction Steps

A mixture of 6-(2,5-difluorophenyl)-5-(6-hydrazinylpyridazin-3-yl)imidazo[2,1-b]oxazole (0.30 g, 0.84 mmol; (prepared using General Procedure A.1 from 1-(2,5-difluorophenyl)ethanone [Matrix], General Procedure B from oxazole-2-amine [GL Synthesis], General Procedure C with NIS, General Procedure I from 1-chloro-4-iodopyridazine (prepared using General Procedure H from 3,6-dichloropyridazine), and General Procedure D with hydrazine hydrate), trimethylacetaldehyde (0.076 g, 0.88 mmol), and glacial acetic acid (1 drop) was dissolved in DCM (6 mL) and MeOH (1 mL) and stirred at ambient temperature for about 1 h. Iodobenzene diacetate (0.28 g, 0.88 mmol) was added and was stirred for about 1 h at ambient temperature. The reaction was diluted with DCM (75 mL) and washed with saturated Na2CO3 solution (150 mL) and water (100 mL). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography using DCM/MeOH (gradient, 97:3 to 90:10). After concentration of the clean fractions, the resulting cream solid was solubilized in hot MeOH, sonicated while cooling, and concentrated under reduced pressure. The resulting solid was dried in a vacuum oven at about 70° C. overnight to provide the title compound as a cream solid (0.22 g, 66%): LC/MS (Table 1, Method a) Rt=2.37 min; MS m/z: 395.2 (M+H)+.

Provenance & Evidence