反应详情

3-Borono-4-methoxybenzoic acid (2.5 g, 12.50 mmol) was dissolved in DMF (6 ml) and 12.50 ml methylamine (2 M solution in THF, 25 mmol) was added followed by HATU (4.75 mg, 12.5 mmol) and NMM (1.375, 12.50 mmol). The reaction mixture was stirred at RT for 20 hours and concentrated. The crude material was added to 50 ml water and extracted 3 times with EtOAc. The combined organic phases were dried (Na2SO4), filtered and concentrated. The crude material was triturated in EtOAc and filtered. The residue was purified by chromatography (Silicagel, CH2Cl2/MeOH 95:5) to give 1.92 g (7.11 mmol, 56.9% yield) of the title compound as a colorless solid. LCMS: (M+H)=210; tR=0.50 min (LC-MS 1). TLC: Rf=0.27 (CH2Cl2/MeOH 95:5). HPLC: tR=3.76 min (HPLC 3). 1H-NMR (d6-DMSO, 600.13 MHz) δ ppm 8.29 (bs, 1H), 8.03 (s, 1H), 7.87 (d, 1H), 7.85 (s, 2H) 7.02 (d, 1H), 3.84 (s, 3H), 2.75 (d, 3H).

1. concentrationconcentrated
2. additionThe crude material was added to 50 ml water
3. extractionextracted 3 times with EtOAc
4. dry with materialThe combined organic phases were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude material was triturated in EtOAc
8. filtrationfiltered
9. customThe residue was purified by chromatography (Silicagel, CH2Cl2/MeOH 95:5)