3-Bromopyridine → HCID 66700982, compound

A solution of 3-bromopyridine (290 μl, 2.96 mmol, 1.20 eq.) in dry THF (9 ml) was added dropwise to a solution of n-BuLi (2.47 ml, 4.94 mmol, 2.0 eq., 2M solution in hexane) in THF (9 ml) at −78° C. and the reaction mixture was stirred at same temperature for 1 h. A solution of 2-benzyl-2-azaspiro[4.5]decan-8-one (600 mg, 2.47 mmol, 1.0 eq.) (see step-6 product AMN-39) in THF (10 ml) was added dropwise at −78° C. and the reaction mixture was stirred at the same temperature for 1 h. After completion of the reaction (monitored by TLC), the reaction mixture was quenched with water (15 ml) while cooling and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with water (20 ml) and brine (20 ml), and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product which was purified by column chromatography (silica gel; 10% MeOH/MC) to yield the desired compound as a light brown semi-solid. Yield: 44% (350 mg, 1.08 mmol).

1. stirringthe reaction mixture was stirred at the same temperature for 1 h
2. customAfter completion of the reaction (monitored by TLC)
3. customthe reaction mixture was quenched with water (15 ml)
4. temperaturewhile cooling
5. extractionextracted with ethyl acetate (2×30 ml)
6. washThe combined organic layers were washed with water (20 ml) and brine (20 ml)
7. dry with materialdried over sodium sulfate
8. customThe solvent was evaporated under reduced pressure
9. customto give the crude product which
10. customwas purified by column chromatography (silica gel; 10% MeOH/MC)

ORD record

ord-84d5967f67934eb2808b3831a338538d

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455475B2