反応 #337756

反応方程式

water

carbonic acid tert-butyl ester 2,4-difluoro-3-formyl-phenyl ester

5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine

potassium hydroxide

→

2,4-difluoro-3-[hydroxy-(5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenol

溶媒

methanol

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate
2. 2
   洗浄The organic layer was washed with brine
3. 3
   乾燥dried over anhydrous sodium sulfate
4. 4
   濃縮concentrated
5. 5
   その他The mixture was purified by silica gel column chromatography
6. 6
   洗浄eluting with 4% methanol in methylene chloride
7. 7
   その他to provide two
8. 8
   その他separate compounds

実験手順

To carbonic acid tert-butyl ester 2,4-difluoro-3-formyl-phenyl ester (39, 0.405 g, 15.7 mmol) in methanol (36 mL), under an atmosphere of nitrogen, was added 5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine (89, 288.0 mg, 14.8 mmol, prepared as described in Example 17) and potassium hydroxide (145.0 mg, 25.9 mmol). The reaction was stirred at room temperature overnight. Then, the reaction was poured into water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The mixture was purified by silica gel column chromatography eluting with 4% methanol in methylene chloride to provide two separate compounds, a colorless oil (P-0009, 0.23 g, 44.1%, MS (ESI) [M+H+]+=354.1), and a colorless oil (P-0042, 0.050 g, 9.2%, MS (ESI) [M+H+]+=367.1).

出典