(NE,R)-N-[[1-(4-chlorophenyl)pyrazol-3-yl]methylidene]-2-methylpropane-2-sulfinamide → (R)-N-((R)-1-(1-(4-chlorophenyl)-1H-pyrazol-3-yl)ethyl)-2-methylpropane-2-sulfinamide

HRID 57442Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10](/[CH:13]=[N:14]/[S@@:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])=[N:9]2)=[CH:4][CH:3]=1.[CH3:21][Mg]Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C@H:13]([NH:14][S@@:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[CH3:21])=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of (R,E)-N-((1-(4-chlorophenyl)-1H-pyrazol-3-yl)methylene)-2-methylpropane-2-sulfinamide (2.12 g, 6.84 mmol) in DCM (40 ml) at −40° C. was added methylmagnesium bromide (9.12 ml, 27.4 mmol). The reaction was stirred at −40° C. for 3 hours. The reaction mixture was then quenched with saturated NH4Cl solution (20 mL). The aqueous layer was adjusted to pH=8 with HCl (1M) and extracted with DCM (2×200 mL). The combined organic was dried (Na2SO4) and concentrated. The residue was then purified via silica gel chromatography (EtOAC/heptane) to give (R)—N—((R)-1-(1-(4-chlorophenyl)-1H-pyrazol-3-yl)ethyl)-2-methylpropane-2-sulfinamide (1.11 g). LCMS (B) m/z 326.3 (M+H)+

Workup

customThe reaction mixture was then quenched with saturated NH4Cl solution (20 mL)
extractionextracted with DCM (2×200 mL)
dry with materialThe combined organic was dried (Na2SO4)
concentrationconcentrated
customThe residue was then purified via silica gel chromatography (EtOAC/heptane)

Sources & evidence

ORD record: ord-80e44b99f69443dc92ed12085a25a1ba
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434719B2

Reaction notes

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