3-BROMOISOXAZOLE-5-CARBOXYLICACID

A solution of methyl 3-bromoisoxazole-5-carboxylate (57.6 mg 0.26 mmol) in THF was added 1M LiOH and stirred at room temperature for 5 h; then, the pH was adjusted with 1M HCl until pH =3, and extracted with EA. Then, it was purified by silica-gel column chromatography; 28.5 mg of General procedure: The relevant acid was treated with oxalyl chloride for under room temperature. Excess thionyl chloride was removed by evaporation. Then, the compound 30 was dissolved in NMP, trimethylamine was added, and the solution was cooled to 0 C. To this stirred suspension, previously prepared acyl chloride was added and stirred at ambient temperature overnight.3-Bromoisoxazole-5-carboxylic acid tert-butyl ester (143 mg, 0.574 mmol, as prepared in the previous step) was dissolved in DCM (1 mL), and TFA (1 mL) was added dropwise. The resulting mixture was stirred at room temperature for 12 h, and the solvent was removed under reduced pressure, to yield a residue, which was used directly in the next step.To a solution of To a solution of S-bromoisoxazole-S-carboxylic acid (2.85 g, 14.8 mmol) in DMF (74 niL) was added 2-(7-aza-lH-benzotriazole-l-yl)-l, l, 3, 3-tetramethyluronium hexafluorophosphate (EtaATU) (6.89 g, 18.1 mmol). The solution was cooled (O0C) and DIPEA (10.5 mL, 60.3 mmol) was added followed by iV, 0-dimethylhydroxylamine hydrochloride (1.81 g, 18.6 mmol) and the reaction was maintained at room temperature. After 25 hours, DMAP (183 mg, 1.50 mmol) was added. After 38 hours, the mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3, saturated aqueous NH4Cl, water, brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with a gradient of 0%-100% EtOAc in heptane to afford Preparation of 3-bromo-5-acetylisoxazole. 4.90 g (202 millimols) of magnesium were added to a solution of 30.9 g (193 millimols) of diethylmalonate, 14.00 g (300 millimols) of ethanol, and 0.9 ml of carbon tetrachloride in ether (176 ml). The mixture was refluxed for 5 hours and then was filtered off; a solution of 36 g (175 millimols) of the chloride of the B. Preparation of

Molecular Weight:191.97
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:190.92181
Monoisotopic Mass:190.92181
Topological Polar Surface Area:63.3
Heavy Atom Count:9
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes