Diisopropylamine → HCID 57975888, compound

Temperature

-20 °C

Diisopropylamine (0.50 ml, 3.54 mmol) and tetrahyrofuran (40 ml) were combined and cooled to −20° C. with stirring. n-Butyl lithium (1.41 ml, 2.5 M in hexanes, 3.53 mmol) was slowly added and stirred at this temperature for 30 minutes. The temperature was decreased to −78 C and neat 5-bromo-2-fluoropyridine (0.38 ml, 3.69 mmol) was added (internal temperature was not allowed to exceed −68 C). The reaction mixture was stirred at −78° C. for 40 minutes. The reaction mixture was added to a solution of 3-methoxy-pyridine-2-carboxylic acid methoxy-methyl-amide (685 mg 3.49 mmol) in tetrahydrofuran (10 ml). This was stirred at −78 C for 1 hour. The reaction mixture was slowly warmed to room temperature, and quenched with saturated aqueous ammonium chloride. The reaction mixture was extracted with dichloromethane, dried over sodium sulfate, and concentrated. The crude product was purified by flash chromatography (0-50% ethyl acetate in hexanes) to give 685 mg (63%) of (5-bromo-2-fluoro-pyridin-3-yl)-(3-methoxy-pyridin-2-yl)-methanone. MS: m/z 310.6+312.9 (M+H+).

1. stirringstirred at this temperature for 30 minutes
2. additionwas added (internal temperature
3. stirringThe reaction mixture was stirred at −78° C. for 40 minutes
4. stirringThis was stirred at −78 C for 1 hour
5. temperatureThe reaction mixture was slowly warmed to room temperature
6. customquenched with saturated aqueous ammonium chloride
7. extractionThe reaction mixture was extracted with dichloromethane
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated
10. customThe crude product was purified by flash chromatography (0-50% ethyl acetate in hexanes)

ORD record

ord-15f3d741f1364883820e056926d49aea

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07626021B2