反应详情

温度

120 °C

N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethoxy)propanamide [Example 34 Step i)] (360 mg), potassium carbonate (203 mg), Pd(Ph3P)4 (42.5 mg) and 4-bromo-1,2-dimethyl-1H-imidazole (193 mg) in MeOH (3 mL) was loaded into a microwave vial, flushed with nitrogen and sealed. The reaction mixture was heated within a Discover microwave at 120° C. for 20 min. After cooling, the mixture was filtered and the filtrate was washed with DCM. Volatiles removed and the residue was purified on silica using 50%-100% EtOAc/iso hexane and then 5% MeOH/DCM to afford the subtitled compound (250 mg). MS [M+H-MeOH]+=426 (MultiMode+) 1H NMR (400 MHz, CDCl3) δ 7.61 and 7.59 (2×s, 1H), 7.53 (d, J=7.7 Hz, 1H), 7.28-7.21 (m, 1H), 7.10-7.03 (m, 2H), 4.62 and 4.37 (2×t, J=5.1 Hz, 1H), 4.26-4.17 and 3.62-3.52 (2×m, 1H), 3.82-3.74 (m, 2H), 3.73-3.64 (m, 2H), 3.60 (s, 3H), 3.41 (s, 3H), 3.38 (s, 3H), 3.37 and 3.29 (2×d, J=4.7 Hz, 2H), 2.94-2.86 (m, 2H), 2.73-2.65 (m, 2H), 2.43 (s, 3H), 1.85-1.73 (m, 2H), 1.73-1.60 (m, 3H), 1.54-1.22 (m, 4H), 1.15-1.01 (m, 1H); a ˜2:1 mixture of rotamers is observed.

1. customflushed with nitrogen
2. customsealed
3. temperatureAfter cooling
4. filtrationthe mixture was filtered
5. washthe filtrate was washed with DCM
6. customVolatiles removed
7. customthe residue was purified on silica using 50%-100% EtOAc/iso hexane