HCID 86721094, compound → HCID 86721093, compound

Temperature

-78 °C

To a solution of (S,E)-N-((4-chloro-3-fluoropyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide (1.03 g, 3.92 mmol) in THF (100 mL) was added allyl magnesium bromide (1 M in ether) (4.70 mL, 4.70 mmol) dropwise and the resulting solution was stirred for 1 h at −78° C. The reaction mixture was then warmed to rt and then quenched with saturated NH4Cl solution. The reaction mixture was extracted with EtOAc (3×). The combined organic layers were concentrated in vacuo, and the residue was then subjected to silica gel purification to provide a mixture of the S and R isomers. MS (ESI) m/z: 305.1 (M+H)+. Chiral separation: AD column eluting with 30% isopropanol in heptane provided peak 1 as the desired (S)—N—((S)-1-(4-Chloro-3-fluoropyridin-2-yl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide (0.710 g, 59%) and peak 2 as (S)—N—((R)-1-(4-chloro-3-fluoropyridin-2-yl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide (0.081 g, 7% yield).

1. temperatureThe reaction mixture was then warmed to rt
2. customquenched with saturated NH4Cl solution
3. extractionThe reaction mixture was extracted with EtOAc (3×)
4. concentrationThe combined organic layers were concentrated in vacuo
5. customthe residue was then subjected to silica gel purification
6. customto provide
7. additiona mixture of the S and R isomers
8. customChiral separation

ORD record

ord-44b34b0174de46af88a39e4735dac235

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901115B2