Methylamine → 3-bromo-6-methyl-5H,6H,7H-pyrrolo[3,4-b]pyridin-7-one

Temperature

70 °C

Methylamine (2M in THF, 9.05 mL) was added to methyl 5-bromo-3-(bromomethyl)picolinate (Example 32, step (i), 1.036 g) in tetrahydrofuran (5 mL) at 20° C. under nitrogen. The resulting suspension was stirred at 70° C. for 30 min. The reaction mixture was cooled and filtered, and the filtrate evaporated to dryness to afford crude product. The crude product was purified by chromatography on silica eluting with ethyl acetate/dichloromethane (5:95 to 100:0). The solid collected during the filtration was dissolved in ethyl acetate and washed with water, extracted with dichloromethane, and then washed with saturated aqueous sodium bicarbonate solution and extracted again with dichloromethane. The combined organic extracts were dried over magnesium sulfate, and then combined with the chromatographed material to afford the sub-titled compound (0.372 g).

1. temperatureThe reaction mixture was cooled
2. filtrationfiltered
3. customthe filtrate evaporated to dryness
4. customto afford crude product
5. customThe crude product was purified by chromatography on silica eluting with ethyl acetate/dichloromethane (5:95 to 100:0)
6. filtrationThe solid collected during the filtration
7. dissolutionwas dissolved in ethyl acetate
8. washwashed with water
9. extractionextracted with dichloromethane
10. washwashed with saturated aqueous sodium bicarbonate solution
11. extractionextracted again with dichloromethane
12. dry with materialThe combined organic extracts were dried over magnesium sulfate

ORD record

ord-9e012ff2f8a64f07aa3e9c7fbc2587ef

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193239B2