Ammonium cerium (IV) nitrate → HCID 11560796, compound

Temperature

55 °C

The compound prepared in Example 6 (501.1 mg, 1.23 mmol) was treated with a saturated sodium bicarbonate solution to obtain 1-benzyl-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (433.6 mg, 1.18 mmol). Ammonium cerium (IV) nitrate (1.94 g, 3.54 mmol) was added at room temperature to a solution of 1-benzyl-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (433.6 mg, 1.18 mmol) in acetic acid (10 ml). The reaction mixture was stirred for 4 hours at 55° C., cooled to room temperature, poured in water, and then extracted with ethyl acetate. The resulting organic layer was washed with a saturated sodium chloride solution, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was dissolved in methanol (20 ml). 2N Lithium hydroxide (5.0 ml) was added to the solution, which was then stirred for 1 hour at room temperature. The reaction mixture was neutralized with 1N hydrochloric acid, concentrated under reduced pressure to discard methanol, and then extracted with ethyl acetate. The resulting organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography to give 1-benzyl-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-3-hydroxymethyl-2-methyl-1H-pyrrolo[3,2-b]pyridine, which was then dissolved in ethyl acetate. The solution was saturated with hydrochloric acid gas and then filtered to give the titled compound as a white solid (69 mg, 13.9%).

1. temperaturecooled to room temperature
2. extractionextracted with ethyl acetate
3. washThe resulting organic layer was washed with a saturated sodium chloride solution
4. dry with materialdried on anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe resulting residue was dissolved in methanol (20 ml)
7. addition2N Lithium hydroxide (5.0 ml) was added to the solution, which
8. stirringwas then stirred for 1 hour at room temperature
9. concentrationconcentrated under reduced pressure
10. extractionextracted with ethyl acetate
11. dry with materialThe resulting organic layer was dried on anhydrous magnesium sulfate
12. concentrationconcentrated under reduced pressure
13. customThe resulting residue was purified with silica gel column chromatography

ORD record

ord-f6fc20d88c494e4db8b172513b4bd8e2

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642269B2