Ammonium Chloride → (R)-N-[(5-bromopyridin-2-yl)(dicyclopropyl)methyl]-2-methylpropane-2-sulfinamide

Isopropylmagnesium chloride (2 M in THF, 1.843 mL, 3.69 mmol) was added dropwise over 5 minutes to a cooled solution of 5-bromo-2-iodopyridine (0.999 g, 3.52 mmol) in THF (7.00 mL) under Ar(g) at 0° C. and then the reaction mixture was stirred for 1 hour. A solution of (R)—N-(dicyclopropylmethylidene)-2-methylpropane-2-sulfinamide (0.715 g, 3.35 mmol) in THF (3.00 mL) was added via syringe over 4 min at 0° C. to the reaction mixture. The reaction mixture was stirred at 0° C. for 1 hour and was warmed to room temperature. Saturated aqueous NH4Cl (15.0 mL) was added to the reaction and extracted with ethyl acetate (30 mL). The organic layer was washed with saturated aqueous NaHCO3, brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0.5-3% methanol in dichloromethane) to yield (R)—N-[(5-bromopyridin-2-yl)(dicyclopropyl)methyl]-2-methylpropane-2-sulfinamide as a yellow oil. MS APCI calc'd for C16H24BrN2OS [M+H]+ 371 and 373. found 371 and 373.

1. stirringThe reaction mixture was stirred at 0° C. for 1 hour
2. extractionextracted with ethyl acetate (30 mL)
3. washThe organic layer was washed with saturated aqueous NaHCO3, brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography (0.5-3% methanol in dichloromethane)

ORD record

ord-c6186f0fda9e48c4bfafc26f46183a2f

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376418B2