反応 #1135848

反応方程式

3-bromo-5-nitropyridin-4-amine

pyridin-3-ylboronic acid

Na2CO3

→

5-nitro-3,3′-bipyridin-4-amine

収率 88.8%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度the solution was refluxed for 15 h until TLC
2. 2
   濃縮concentrated under reduced pressure
3. 3
   濃縮The reaction mixture was concentrated
4. 4
   抽出The organic extract
5. 5
   洗浄was washed with water
6. 6
   その他dried
7. 7
   濃縮concentrated under vacuum
8. 8
   その他The crude product was purified on a silica gel column (100% EtOAc→2:98 MeOH:DCM)

実験手順

A solution of 3-bromo-5-nitropyridin-4-amine (XIII) (6 g, 26 mmol), pyridin-3-ylboronic acid (3.54 g, 29 mmol), 1 N Na2CO3 solution (78 ml) and 1,4-dioxane (150 mL) was degassed with argon thrice. Pd(PPh3)2Cl2 (927 mg, 5 mmol %) was added to the reaction and the solution was refluxed for 15 h until TLC showed the reaction was complete. The reaction was passed through a pad of Celite and then concentrated under reduced pressure. The reaction mixture was concentrated and the residue was taken up in ethyl acetate. The organic extract was washed with water, dried and concentrated under vacuum. The crude product was purified on a silica gel column (100% EtOAc→2:98 MeOH:DCM) to give 5-nitro-3,3′-bipyridin-4-amine (XIV) as a yellow solid (5 g, 23.1 mmol, 87% yield). 1H NMR (CDCl3, 400 MHz,) δ ppm 9.31 (s, 1H), 8.80-8.79 (m, 1H), 8.70 (s, 1H), 8.23 (s, 1H), 7.80-7.73 (m, 1H), 7.52-7.48 (m, 1H). ESIMS found C10H8N4O2 m/z 216.95 (M+H).

出典