反应详情

温度

85 °C

In a 50 mL round-bottomed flask, dimethylamine hydrochloride (4.91 g, 60.3 mmol, Eq: 6) was added to 37% aqueous formaldehyde (4.49 mL, 60.3 mmol, Eq: 6). Ethyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate (1.91 g, 10.0 mmol, Eq: 1.00) in ethanol (50 mL) was added followed by acetic acid (5.00 mL, 87.3 mmol, Eq: 8.7). The reaction mixture was heated to 85° C. and stirred over the weekend. The crude reaction mixture was filtered through a pad of Celite, concentrated in vacuo to ˜20% of its original volume, water (100 mL) was added, and this was then washed with DCM (50 mL). The aqueous layer was cooled, basified to pH 11 through the addition of 3 M aqueous NaOH and extracted with DCM. The organic layers were dried over Na2SO4 and concentrated in vacuo to give 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester as light yellow solid (1.9 g), m/z=248 (M+H).

1. customThe crude reaction mixture
2. filtrationwas filtered through a pad of Celite
3. concentrationconcentrated in vacuo to ˜20% of its original volume, water (100 mL)
4. additionwas added
5. washthis was then washed with DCM (50 mL)
6. temperatureThe aqueous layer was cooled
7. additionbasified to pH 11 through the addition of 3 M aqueous NaOH
8. extractionextracted with DCM
9. dry with materialThe organic layers were dried over Na2SO4
10. concentrationconcentrated in vacuo