Реакция #88533

Уравнение реакции

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

Растворители

pyridine

Условия реакции

Обработка

1. 1
   Температураto cool to ambient temperature
2. 2
   Другоеthen evaporated in-vacuo
3. 3
   workup.ADDITIONThe resultant residue was treated with saturated aqueous sodium carbonate solution (15 mL)
4. 4
   Фильтрацияthe resultant solid collected by filtration
5. 5
   Промывкаwashed with water (20 mL)
6. 6
   ЭкстракцияThe filtrate was extracted with 20% methanol in dichloromethane (6×25 mL)
7. 7
   Концентрированиеconcentrated in-vacuo

Методика

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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