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

HRID 1374170Notes

Reaction equation

HRID 1374170 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-e75f3624da3b4b67a055a0a13d0f6b9a
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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