5-Bromopyridine-2-carbaldehyde → (NE,R)-N-[(5-bromo-2-pyridinyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 2038780Notes

Reaction equation

HRID 2038780 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=O)=[N:13][CH:14]=1>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[Br:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:15]=[N:7]/[S@@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 98775625-Bromopyridine-2-carbaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 58438195(NE,R)-N-[(5-bromo-2-pyridinyl)methylidene]-2-methylpropane-2-sulfinamideYield 97.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-(+)-2-methyl-2-propanesulfinamide (2.60 g, 21.5 mmol) in 100 mL of CH2Cl2 at room temperature was added CuSO4 (7.53 g, 47.2 mmol) and 5-bromo-pyridine-2-carbaldehyde (4.39 g, 23.6 mmol). The reaction mixture was stirred at room temperature for 21 h and then filtered through Diatomaceous earth, washing with CH2Cl2. The filtrates were concentrated to give a pale brown oil that was purified by flash chromatography on silica gel, eluting with 10-25% EtOAc in hexanes, to afford 6.04 g (97%) of (R)-2-methyl-propane-2-sulfinic acid 1-(5-bromo-pyridin-2-yl)-meth-(E)-ylideneamide as a pale yellow solid.

Workup

  1. filtrationfiltered through Diatomaceous earth
  2. washwashing with CH2Cl2
  3. concentrationThe filtrates were concentrated
  4. customto give a pale brown oil that
  5. customwas purified by flash chromatography on silica gel
  6. washeluting with 10-25% EtOAc in hexanes

Sources & evidence

ORD record
ord-ad04ed62e6084308b85e2b954c33f2b9
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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