Sulfuric acid magnesium salt (1:1) → (NE)-N-[(5-bromo-3-fluoro-2-pyridinyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1711489Notes

Reaction equation

HRID 1711489 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:10]=[C:11]([F:17])[C:12]([CH:15]=O)=[N:13][CH:14]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[C:11]([F:17])[C:12](/[CH:15]=[N:7]/[S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 210758705-Bromo-3-fluoropyridine-2-carbaldehyde

Product 1

HCID 21075886(NE)-N-[(5-bromo-3-fluoro-2-pyridinyl)methylidene]-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-(+)-2-methyl-2-propanesulfinamide (9.898 g, 81.67 mmol) in CH2Cl2 (160 mL) was added 5-bromo-3-fluoropyridine-2-carbaldehyde (16.66 g, 81.67 mmol), pyridinium p-toluenesulfonate (1.026 g, 4.08 mmol), and magnesium sulfate (49.15 g, 408.3 mmol). The reaction was stirred at room temperature overnight, then filtered through celite and concentrated in vacuo. The residue was subjected to silica gel chromatography eluted with 0 to 10% ethyl acetate in hexanes to provide N-[(1E)-(5-bromo-3-fluoropyridin-2-yl)methylidene]-2-methylpropane-2-sulfinamide that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 307.0 for M+H+(81Br).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. washeluted with 0 to 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d59e0e9f6c14423b84d088bcb4e3b27f
Source dataset
uspto-grants-2010_09
Patent number
US07790754B2

Reaction notes

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