Methanol → HCID 23614996, compound

Participants

Reaction Conditions

Reaction Steps

Quinoxalinone vii (420 mg, 1.14 mmol) was dissolved in dry CH2Cl2 (10 mL) and cooled to −78° C. under an atmosphere of N2. BBr3 (536 μL, 5.68 mmol) was added dropwise. After the addition, the reaction mixture was warmed to room temperature and stirred for 2 h. The mixture was cooled to −78° C. and MeOH (3 mL) was added to quench the reaction. The mixture was concentrated under reduced pressure and then diluted with water (30 mL) and extracted with EtOAc (7×50 mL). The organic layers were combined and solvent was removed under reduced pressure to provide crude product (350 mg) as a yellow solid. A small portion of the crude material was purified by reverse phase preparative HPLC for characterization, the rest of the crude was used directly for the next step without any further purification. 1H NMR (CD3OD) δ 8.74 (d, J=9 Hz, 1H), 7.14 (d, J=9 Hz, 1H), 7.13 (t, J=9 Hz, 1H), 6.74 (d, J=9 Hz, 1H), 6.72 (d, J=9 Hz, 1H), 1.33 (s, 6H). Anal. Calcd for C17H14N2O4 ⅙CF3COOH: C, 63.22; H, 4.34; N, 8.51. Found: C, 63.54; H, 4.50; N, 8.32.

Provenance & Evidence