反応 #452986

反応方程式

5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine

sodium carbonate

1-naphthaleneboronic acid

sodium bicarbonate

→

oil

収率 62.0%

5-(1-Naphthalenyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine

収率 62.0%

溶媒

benzene

Water

反応条件

後処理

1. 1
   温度The reaction mixture was refluxed overnight
2. 2
   抽出The mixture was extracted with EtOAc, which
3. 3
   乾燥was dried over MgSO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The residue was chromatographed on a silica gel column
7. 7
   洗浄eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90

実験手順

To a solution of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine (272 mg, 1.00 mmol) in benzene (2.0 mL) were added aqueous sodium carbonate (2.0M, 1.0 mL), tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.03 mmol) and 1-naphthaleneboronic acid (189 mg, 1.10 mmol). The reaction mixture was refluxed overnight, then cooled to room temperature. Water (2 mL) was added, and solid sodium bicarbonate was added until the aqueous layer was saturated. The mixture was extracted with EtOAc, which was dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column, eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90 to afford a light yellowish oil (196 mg, 62%). MS (CI/NH3) m/z 319 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.71-1.92 (m, 3H), 2.00-2.10 (m, 1H), 2.27-2.38 (m, 1H), 2.51 (s, 3H), 2.66-2.75 (m, 1H), 3.09-3.17 (m, 1H), 3.98-4.14 (m, 2H), 7.34-7.57 (m, 5H), 7.72-7.96 (m, 3H),8.36-8.43 (m, 1H).

出典