反応 #2201230

反応方程式

azaindole

3-Iodo-5-(2-phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

benzenesulfonyl chloride

sodium hydroxide

→

azaindole

収率 68.0%

1-Benzenesulfonyl-3-iodo-5-(2-phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

収率 68.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONwas sequentially added
2. 2
   その他was partitioned between dichloromethane and saturated brine
3. 3
   抽出The organic extract
4. 4
   乾燥was dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated

実験手順

To a solution of the crude azaindole 26 (prepared in the previous step) in dichloromethane (373 mL) was sequentially added, benzenesulfonyl chloride (12.6 mL, 99.1 mmol), 50% aqueous sodium hydroxide (12.2 mL) and tetrabutylammonium hydrogen sulfate (2.82 g, 8.3 mmol). After 2 h stirring the mixture was partitioned between dichloromethane and saturated brine. The organic extract was dried (MgSO4), filtered and concentrated to afford the azaindole 27 (24.2 g, 68% from 25) as a tan coloured solid. 1H NMR (400 MHz; CDCl3) δ 6.89-6.92 (m, 2H), 7.01-7.05 (m, 2H), 7.22-7.28 (m, 3H), 7.33-7.37 (m, 1H), 7.45 (dd, J=7.6, 2.0 Hz, 1H), 7.47-7.52 (m, 2H), 7.60 (tt, J=7.6, 1.3 Hz, 1H), 7.84 (d, J=2.0 Hz, 1H), 7.85 (s, 1H), 8.20-8.22 (m, 2H) and 8.64 (d, J=2.0 Hz, 1H).

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