indium(III)chloride → (S)-N-((S)-1-(4-Chloropyridin-2-yl)but-3-enyl)-2-methylpropane-2-sulfinamide

To a cooled (0-5° C.) mixture of indium(III) chloride (13.56 g, 61.3 mmol) in tetrahydrofuran (170 mL) was added dropwise over 30 min. allylmagnesium bromide (1M in diethylether) (62 mL, 61.3 mmol). The reaction was allowed to warm to rt. After 1 h at rt, a solution of 1A (10 g, 40.9 mmol) in ethanol (170 mL) was added. After 2-3 h, the reaction was concentrated under vacuum at 50-55° C. The crude material was partitioned between ethyl acetate (200 ml) and water (1×50 ml) and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×50 ml). The organic layers were combined and washed with brine (1×100 ml), dried over sodium sulfate, filtered and concentrated to give 1B (13.5 g, 106%) as a yellow oil. MS (ESI) m/z: 287.2 (M+H)+. This material was used in the next step without further purification.

1. temperatureTo a cooled
2. waitAfter 2-3 h
3. concentrationthe reaction was concentrated under vacuum at 50-55° C
4. customThe crude material was partitioned between ethyl acetate (200 ml) and water (1×50 ml)
5. customthe layers were separated
6. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
7. washwashed with brine (1×100 ml)
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-44df7cb44075484c85184a2a0b2d1e9a

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409908B2