Lithium Hexamethyldisilazide → (NZ)-N-[2-(benzenesulfonyl)-1-(3-bromophenyl)-2-fluoroethylidene]-2-methylpropane-2-sulfonamide

HRID 1527515Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[N:9]\[S:10]([C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.[F:17][CH2:18][S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[C:22]1([S:19]([CH:18]([F:17])/[C:8](=[N:9]\[S:10]([C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:12])=[O:11])/[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)(=[O:21])=[O:20])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a mixture of 2-methyl-propane-2-sulfonic acid 1-(3-bromo-phenyl)-meth-(Z)-ylideneamide (2.16 g, 7.49 mmol) and (fluoromethylsulfonyl)benzene (1.31 g, 7.49 mmol) in THF (50 mL), cooled to −78° C., was added LiHMDS (1M in THF; 7.87 mL, 7.87 mmol). The reaction mixture was stirred for 40 min at −78° C., followed by quenching saturated aqueous NH4Cl (10 mL) at −78° C. The mixture was extracted with EtOAc (3×), dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash column chromatography on silica gel (c-hexane/EtOAc 3:1) afforded the title compound. MS (LC/MS): 462/464 [M+H]+; tR (HPLC conditions f): 2.20 min.

Workup

customby quenching saturated aqueous NH4Cl (10 mL) at −78° C
extractionThe mixture was extracted with EtOAc (3×)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash column chromatography on silica gel (c-hexane/EtOAc 3:1)

Sources & evidence

ORD record: ord-a6277f41879d40d2ad1d1623ef665759
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085555B2

Reaction notes

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