反应详情

温度

70 °C

A mixture of 5.50 g (19 mmol) of Na2CO3×10H2O, 100 ml of water and 30 ml of methanol was purged with argon for 30 min. The obtained solution was added to a mixture of 2.60 g (7.7 mmol) of 2-methyl-N-[3-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]aniline, 2.68 g (7.7 mmol) of N-[(6-bromopyridin-2-yl)methyl]-2,6-diisopropylaniline, and 0.44 g (0.39 mmol) of Pd(PPh3)4 in 120 ml of toluene. This mixture was stirred for 12 h at 70° C., then cooled to room temperature. The organic layer was separated, the aqueous layer was extracted with 3×50 ml of ethyl acetate. The combined organic extract was washed with brine, dried over Na2SO4, and evaporated to dryness. The residue was purified by flash chromatography on silica gel 60 (40-63 um; eluent: hexane-triethylamine=20:1, vol.). Yield 2.10 g (57%) of white crystalline solid. Anal. calc. for C33H39N3: C, 82.97; H, 8.23; N, 8.80. Found: C, 83.19; H, 8.45; N, 8.62. 1H NMR (CDCl3): δ 7.71 (m, 1H), 7.37 (m, 1H), 7.28-7.32 (m, 2H), 7.22-7.26 (m, 2H), 7.00-7.13 (m, 5H), 6.61 (m, 1H), 6.47 (m, 1H), 4.25 (s, 2H), 4.10 (s, 2H), 3.98 (br.s, 1H), 3.82 (br.s, 1H), 3.31 (s, J=6.9 Hz, 2H), 2.14 (s, 3H), 2.09 (s, 3H), 1.21 (d, J=6.9 Hz, 12H).

1. customwas purged with argon for 30 min
2. temperaturecooled to room temperature
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with 3×50 ml of ethyl acetate
5. extractionThe combined organic extract
6. washwas washed with brine
7. dry with materialdried over Na2SO4
8. customevaporated to dryness
9. customThe residue was purified by flash chromatography on silica gel 60 (40-63 um; eluent: hexane-triethylamine=20:1, vol.)