Diethyl Ether → HCID 69679626, compound

To a solution of 5-bromopicolinaldehyde (2.0 g, 10.8 mmol) in THF (20 mL) was added 3.0 M solution of ethyl magnesium bromide in diethyl ether (7.1 ml, 21.5 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 6 h. The reaction mixture was quenched with saturated ammonium chloride solution (20 mL) and water (15 mL), extracted with ethyl acetate (200 mL), dried over sodium sulphate and concentrated under reduced pressure to obtain crude product. The crude product was purified by a Biotage Isolera® One column (using 10% ethyl acetate and hexane (0.72 g, (45% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.57 (d, 1H), 8.01-7.98 (dd, 1H), 7.445 (d, 1H), 5.36 (d, 1H), 4.49-4.45 (dd, 1H), 1.65-1.61 (m, 2H), 0.815 (t, 3H).

1. customThe reaction mixture was quenched with saturated ammonium chloride solution (20 mL) and water (15 mL)
2. extractionextracted with ethyl acetate (200 mL)
3. dry with materialdried over sodium sulphate
4. concentrationconcentrated under reduced pressure
5. customto obtain crude product
6. customThe crude product was purified by a Biotage Isolera® One column (

ORD record

ord-47852b401ae543ef8fbf8ce3ee219ff4

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2