Triisopropyl borate → HCID 67465561, compound

Participants

Reaction Conditions

Reaction Steps

Butyl lithium (2.5 M in THF, 6.08 mL, 2.5 equiv.) was added dropwise into a stirring solution of 7-bromo-2-methyl-2,3-dihydro-pyrido[3,2-b][1,4]oxazine-4-carboxylic acid tert-butyl ester (2.0 g, 6.08 mmol, 1.0 equiv.) and triisopropylborate (2.86 g, 15.19 mmol, 2.5 equiv.) in anhydrous THF (20 mL) at −78° C. under nitrogen. The reaction was stirred at −78° C. and monitored with LCMS. After 2 hr, LCMS indicated the reaction complete. The reaction was quenched with water (20 mL) and concentrated under reduced pressure. The residue was washed with ether (2×10 mL) and the aqueous layer was placed in an ice-water bath. While stirring, 10 N HCl aqueous solution was carefully added dropwise until pH˜7. Filtration and washing with ice-water (3×5 mils) gave the desired product as a white solid (923 mg).

Provenance & Evidence