反应详情

温度

-78 °C

A solution of 4-bromo-5-isopropyl-1H-indazole (116 g, 6.9 mmol) in Et2O (4 mL) is added slowly to a suspension of KH (1.0 g of 30% dispersion in mineral oil, 7.7 mmol) in Et2O (20 mL) at 0° C. and the mixture is stirred for 20 minutes. After cooling to −78° C., t-BuLi (8.9 mL of 1.7 M in Hex, 15 mmol) is added and the resulting mixture is stirred for 40 minutes at −78° C. To this is added B(On-Bu)3 (5.6 mL, 21 mmol) and the mixture is stirred for 24 hours at room temperature. The reaction mixture is quenched with 1N H3PO4 and extracted with Et2O— The combined Et2O layers are back-extracted with 1N NaOH (3×10 mL). The combined NaOH extracts are acidified with 1N H3PO4 and extracted with EtOAc. The EtOAc extracts are washed with saturated brine, dried (MgSO4), and concentrated to yield 5-isopropyl-1H-indazole-4-boronic acid. 1H NMR (CDCl3) 7.85 (s, 1H), 7.42 (d, 1H), 7.37 (d, 1H), 3.6 (br s, 2H), 2.88 (m, 1H), 1.32 (d, 6H).

1. stirringthe resulting mixture is stirred for 40 minutes at −78° C
2. stirringthe mixture is stirred for 24 hours at room temperature
3. customThe reaction mixture is quenched with 1N H3PO4
4. extractionextracted with Et2O— The combined Et2O layers
5. extractionare back-extracted with 1N NaOH (3×10 mL)
6. extractionextracted with EtOAc
7. washThe EtOAc extracts are washed with saturated brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated