tert-Butylsulfinamide, (S)-(-)- → (S)-N-(5-bromo-6-(((tert-butylsulfinyl)imino)methyl)pyridin-2-yl)acetamide

HRID 2170308

Reaction equation

HRID 2170308 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:10][C:11](=[O:13])[CH3:12])=[N:6][C:7]=1[CH:8]=O.[CH3:14][C:15]([S@@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:10][C:11](=[O:13])[CH3:12])=[N:6][C:7]=1[CH:8]=[N:20][S@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19]

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 90280237N-(5-Bromo-6-formyl-2-pyridinyl)acetamide

Product 1

HCID 90280385(S)-N-(5-bromo-6-(((tert-butylsulfinyl)imino)methyl)pyridin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Copper(II) sulfate (anhydrous 2.8 g, 17.2 mmol) was added to a solution of N-(5-bromo-6-formylpyridin-2-yl)acetamide (crude material, assume 8.6 mmol) and (S)-2-methylpropane-2-sulfinamide (1.2 g, 9.4 mmol) in DCM (30 ml). The suspension was stirred overnight at room temperature. The reaction was filtered and washed with DCM (3×20 ml). The filtrate was concentrated. The crude product was purified by flash column (30% EtOAc/Hexanes). MS (m/z) 346.1 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. washwashed with DCM (3×20 ml)
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by flash column (30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-32e67f315d79418688dd525d9f8d0186
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Linked notes

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