18-Crown-6 → HCID 67997695, compound

Commercially available (5-bromopyridin-2-yl)methanol (2000 mg, 10.6 mmol) in CH2Cl2 (20 mL) is treated with di-isopropylethylamine (2.8 mL, 16 mmol) and methane sulfonylchloride (1.0 mL, 12.8 mmol) stirred for 1 hour and the solvent removed under reduced pressure. The crude solid is dissolved in dimethylformamide (10 mL) and treated with sodium methanesulfinate (4.39 g, 42.5 mmol), 18-crown-6 (580 mg, 2.13 mmol) and the mixture stirred at room temperature for 16 hours. The reaction mixture is diluted with ethyl acetate (20 mL), washed with water (20 mL) and brine(20 mL), dried over MgSO4, filtered, concentrated, and the crude material purified by column chromatography on silica gel eluting with a gradient of ethyl acetate/heptane to afford the title compound (2.12 g): m/z (Cl) 251 [M+H].

1. customthe solvent removed under reduced pressure
2. dissolutionThe crude solid is dissolved in dimethylformamide (10 mL)
3. stirringthe mixture stirred at room temperature for 16 hours
4. washwashed with water (20 mL) and brine(20 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customthe crude material purified by column chromatography on silica gel eluting with a gradient of ethyl acetate/heptane

ORD record

ord-25eeda38859d41b696dbcdd58e2454a4

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206126B2