4-Cyanopyridine → 1-(Pyridin-4-yl)cyclopropanaMine

To 4-cyanopyridine (1.04 g, 10 mmol) in diethyl ether (50 mL), tetraisopropoxytitanium (3.27 mL, 11 mmol) and ethylmagnesium bromide (6.3 mL, 22 mmol, 3 M in diethyl ether) were added dropwise in a nitrogen stream at −78° C., and after 10 minutes, the reaction solution was warmed to room temperature and stirred for 1.5 hours and then stirred with a borane-tetrahydrofuran complex (21.5 mL, 20 mmol. 0.93 M in tetrahydrofuran) for 1 hour. After completion of the reaction, the reaction solution was diluted with diethyl ether (10 mL), and dilute hydrochloric acid (30 mL, 1 M) was added dropwise. After addition of aqueous sodium hydroxide (100 mL, 10% w/v), the reaction solution was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give the desired product (2.6% yield).

1. customAfter completion of the reaction
2. additionwas added dropwise
3. extractionthe reaction solution was extracted with ethyl acetate
4. dry with materialthe extract was dried over anhydrous sodium sulfate
5. customevaporated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

ORD record

ord-7de688e398844ed0875cfbd34438ebe9

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440666B2