Hydrochloric Acid → 1-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-carbaldehyde

Sodium hydride (60%, 23 mg, 0.562 mmol) and allyl bromide (36 μl, 0.413 mmol) were added at 0° C. to a solution of 7-dibutoxymethyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine (0.109 g, 0.375 mmol) prepared in Step 3 in anhydrous tetrahydrofuran (3 ml). The reaction mixture was stirred for 1 hour at room temperature and water (1 ml) was added thereto. The reaction mixture was extracted with ethyl acetate (10 ml), dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. Tetrahydrofuran (10 ml) was added to the resulting residue. 0.5N hydrochloric acid (3 ml, 1.5 mmol) was added to the reaction mixture, which was then refluxed overnight. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, basified with a saturated sodium bicarbonate solution, extracted with ethyl acetate (20 ml), dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5, v/v) to give 50 mg of the titled compound as yellow oil.

1. extractionThe reaction mixture was extracted with ethyl acetate (10 ml)
2. dry with materialdried on anhydrous magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. additionTetrahydrofuran (10 ml) was added to the resulting residue
5. temperaturewas then refluxed overnight
6. temperatureThe reaction mixture was cooled to room temperature
7. concentrationconcentrated under reduced pressure
8. extractionextracted with ethyl acetate (20 ml)
9. dry with materialdried on anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5

ORD record

ord-8ee5c04fd4f248248df352815d32e037

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188114B2