Benzyl mercaptan → HCID 59192525, compound

A solution of phenyl-methanethiol (0.8 mL, 5.84 mmol) in DMF (5 mL) was treated with NaH (0.140 g, 5.84 mmol) at room temperature under argon. After 15 min of stirring, the reaction mixture was treated with a solution of 2-chloro-5-(3-isopropyl-phenyl)-pyridine (0.900 g, 3.90 mmol) in DMF (15 mL). After 2 h of additional stirring at room temperature (reaction was monitored by TLC), the reaction mixture was quenched with ice cold water (20 mL), and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (2×10 mL), dried over Na2SO4, and concentrated in vacuo to obtain a crude product, which was purified over silica gel (Biotage column chromatography, gradient elution using 0-1% ethyl acetate in hexane) to furnish 2-benzylsulfanyl-5-(3-isopropyl-phenyl)-pyridine (0.680 g, 54.71%).

1. stirringAfter 2 h of additional stirring at room temperature
2. custom(reaction was monitored by TLC)
3. customthe reaction mixture was quenched with ice cold water (20 mL)
4. extractionextracted with ethyl acetate (3×10 mL)
5. washThe combined organic layers were washed with water (2×10 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. customto obtain a crude product, which
9. customwas purified over silica gel (Biotage column chromatography, gradient elution using 0-1% ethyl acetate in hexane)

ORD record

ord-545aed259c174fc784479a6062e46aa1

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263656B2