Lithium Hexamethyldisilazide → HCID 67254506, compound

Participants

Reaction Conditions

Reaction Steps

[6-(5-Cyano-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (100 mg, 0.28 mmol) was dissolved in THF (4 mL) and cooled to 0° C. To this was added LHMDS (1M in THF, 0.28 mL, 0.28 mmol) and stirred at 0° C. for 1 h. Another portion of LHMDS (1M in THF, 0.28 mL, 0.28 mmol) was added at 0° C. The reaction was stirred at 0° C. for 2 h and was allowed to warm up to room temperature. The reaction was stirred at room temperature for 6 h. The solvent was removed. Preparative HPLC (C18 column) gave the title compound (33 mg, 36%) as a white solid. MS (ESI) m/z: 326 [M+1]+; 1H NMR (300 MHz, CD3OD) δ 8.56 (1H, s), 8.50 (1H, s), 7.28 (1H, s), 7.15 (1H, s), 5.65 (1H, dd), 3.18 (1H, dd), 2.35 (3H, s), 2.30 (1H, m).

Provenance & Evidence