Benzyl Bromide → HCID 67141638, compound

18-Crown-6 (26 mg, 0.098 mmol) and potassium tert-butoxide (253 mg, 2.25 mmol) were added to a solution of 2,3-dimethyl-7-(4-methylsulfanylphenyl)-1H-pyrrolo[2,3-c]pyridine (300 mg, 0.98 mmol) prepared in Example 262 in anhydrous tetrahydrofuran (9 ml). The reaction mixture was stirred for 30 minutes at room temperature and benzyl bromide (175 μl, 1.47 mmol) was added thereto. The reaction mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate and water was added thereto. The separated organic layer was dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography. The resulting pale yellow solid (242 mg, 0.67 mmol) was dissolved in 6 ml of acetic acid. Ammonium cerium (IV) nitrate (1.11 g, 2.01 mmol) was added at room temperature to the resulting solution, which was stirred for 3 hours at 55° C. and then cooled to room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer 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 (11 ml) and 2N lithium hydroxide (3 ml) was added thereto. The reaction mixture was stirred for 1 hour at room temperature, neutralized with 1N hydrochloric acid, and then concentrated under reduced pressure. The resulting residue was extracted with ethyl acetate. The 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 obtain 1-benzyl-3-hydroxymethyl-2-methyl-7-(4-methylsulfanylphenyl)-1H-pyrrolo[2,3-c]pyridine. The product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 48 mg of the titled compound as a white solid.

1. stirringThe reaction mixture was stirred overnight
2. additionwas added
3. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe resulting residue was purified with silica gel column chromatography
6. stirringwas stirred for 3 hours at 55° C.
7. temperaturecooled to room temperature
8. extractionwas then extracted with ethyl acetate
9. washThe organic layer washed with a saturated sodium chloride solution
10. dry with materialdried on anhydrous magnesium sulfate
11. concentrationconcentrated under reduced pressure
12. dissolutionThe resulting residue was dissolved in methanol (11 ml)
13. addition2N lithium hydroxide (3 ml) was added
14. stirringThe reaction mixture was stirred for 1 hour at room temperature
15. concentrationconcentrated under reduced pressure
16. extractionThe resulting residue was extracted with ethyl acetate
17. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
18. concentrationconcentrated under reduced pressure
19. customThe resulting residue was purified with silica gel column chromatography

ORD record

ord-97f235d8002641f29aa11e860563342a

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662832B2