反応 #2150558

反応方程式

2-bromo-6-benzyloxypyridine

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

sodium tert-butoxide

→

desired product

収率 65.0%

6-(benzyloxy)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboro-lan-2-yl)phenyl)pyridin-2-amine

収率 65.0%

溶媒

tert-butyl alcohol

反応条件

後処理

1. 1
   その他The reaction mixture was purged with nitrogen for a few minutes
2. 2
   その他The reaction was quenched with 10% aqueous citric acid
3. 3
   workup.ADDITIONpoured into ethyl acetate
4. 4
   洗浄The organic layer was washed with water and brine
5. 5
   乾燥dried (Na2SO4)
6. 6
   ろ過filtered
7. 7
   その他evaporated in vacuo
8. 8
   その他The resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 100% ethyl acetate in heptane)

実験手順

To a mixture of 2-bromo-6-benzyloxypyridine (1.10 g, 4.15 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.00 g, 4.57 mmol, 1.1 eq.) in tert-butyl alcohol (20 mL) was added sodium tert-butoxide (556 mg, 5.78 mmol, 1.40 eq.), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (98 mg, 0.25 mmol, 0.06 eq.), and bis(dibenzylideneacetone)palladium(0) (96 mg, 0.17 mmol, 0.04 eq.). The reaction mixture was purged with nitrogen for a few minutes, and the dark orange reaction mixture was heated under microwave irradiation (300 watts, 120° C.) for 15 minutes. The reaction was quenched with 10% aqueous citric acid and poured into ethyl acetate. The organic layer was washed with water and brine, then dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 100% ethyl acetate in heptane) to give the desired product (l-1) (1.08 g, 65% yield) as slightly brown solid. 1H NMR (CDCl3, 400 MHz) δ ppm 7.75 (d, J=8.4 Hz, 2H), 7.49 to 7.41 (m, 3H), 7.41 to 7.34 (m, 4H), 7.34 to 7.27 (m, 1H), 6.46 (s, 1H), 6.44 (d, J=7.9 Hz, 1H), 6.30 (d, J=7.9 Hz, 1H), 5.37 (s, 2H), 1.34 (s, 12H).

出典