反応 #88532

反応方程式

Thionyl chloride

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

methanol

→

title compound

収率 99.0%

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

収率 99.0%

反応条件

後処理

1. 1
   温度a cooled
2. 2
   workup.ADDITIONOn complete addition
3. 3
   温度the mixture was heated
4. 4
   温度under reflux for 66 hours
5. 5
   その他evaporated
6. 6
   その他The resultant residue was azeotroped with toluene (2×150 mL)

実験手順

Thionyl chloride (27.5 mL) was added dropwise over 15 minutes to a cooled (0° C.) suspension of 2-amino-3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-propionic acid hydrochloride (7.28 g, 22.3 mmol) in methanol (150 mL). On complete addition, the mixture was heated under reflux for 66 hours. The mixture was allowed to cool to ambient temperature and evaporated. The resultant residue was azeotroped with toluene (2×150 mL) to afford the title compound as a fawn solid (7.7 g, 99%). 1H NMR (400 MHz, DMSO-d6): 12.06 (s, 1H), 8.39 (s, 3H), 8.17 (d, J=5.2 Hz, 1H), 7.50 (d, J=2.5 Hz, 1H), 7.19 (d, J=5.2 Hz, 1H), 4.07-4.06 (m, 1H), 3.54 (dd, J=14.9, 5.8 Hz, 1H), 3.30 (dd, J=14.9, 9.0 Hz, 1H).

出典