반응 #88533

반응 방정식

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

용매

pyridine

반응 조건

후처리

1. 1
   온도to cool to ambient temperature
2. 2
   기타then evaporated in-vacuo
3. 3
   workup.ADDITIONThe resultant residue was treated with saturated aqueous sodium carbonate solution (15 mL)
4. 4
   여과the resultant solid collected by filtration
5. 5
   세척washed with water (20 mL)
6. 6
   추출The filtrate was extracted with 20% methanol in dichloromethane (6×25 mL)
7. 7
   농축concentrated in-vacuo

실험 절차

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).

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