反応 #88533

反応方程式

2-amino-3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-propionic acid methyl ester

formaldehyde

→

title compound

4-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester

溶媒

pyridine

反応条件

後処理

1. 1
   温度to cool to ambient temperature
2. 2
   その他then evaporated in-vacuo
3. 3
   workup.ADDITIONThe resultant residue was treated with saturated aqueous sodium carbonate solution (15 mL)
4. 4
   ろ過the resultant solid collected by filtration
5. 5
   洗浄washed with water (20 mL)
6. 6
   抽出The filtrate was extracted with 20% methanol in dichloromethane (6×25 mL)
7. 7
   濃縮concentrated in-vacuo

実験手順

A suspension of 2-amino-3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-propionic acid methyl ester (3.5 g, 10 mmol) in pyridine (25 mL) was treated with formaldehyde solution (37% in water, 0.90 mL) and the resulting mixture was heated to 100° C. for 1.25 hours. The mixture was allowed to cool to ambient temperature then evaporated in-vacuo. The resultant residue was treated with saturated aqueous sodium carbonate solution (15 mL) and the resultant solid collected by filtration and washed with water (20 mL). The filtrate was extracted with 20% methanol in dichloromethane (6×25 mL). The combined organic phase was combined with solid and concentrated in-vacuo to afford the title compound as a brown residue (2.1 g, 87%). LCMS (Method B): RT=2.36 min, M+H+=266. 1H NMR (400 MHz, DMSO-d6): 11.66 (s, 1H), 8.02 (d, J=5.2 Hz, 1H), 7.06 (d, J=5.1 Hz, 1H), 4.01-3.71 (m, 3H), 3.69 (s, 3H), 3.19 (dd, J=15.4, 4.7 Hz, 1H), 2.94 (dd, J=15.4, 8.9 Hz, 1H).

出典