tert-Butylsulfinamide, (S)-(-)- → (NZ,S)-N-[[3-bromo-5-(1,3-dioxoisoindol-2-yl)-2-pyridinyl]methylidene]-2-methylpropane-2-sulfinamide

HRID 2170360Notes

Reaction equation

HRID 2170360 reaction equation
[Br:1][C:2]1[C:3]([CH:19]=O)=[N:4][CH:5]=[C:6]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH:7]=1.[CH3:21][C:22]([S@@:25]([NH2:27])=[O:26])([CH3:24])[CH3:23]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[C:3](/[CH:19]=[N:27]\[S@:25]([C:22]([CH3:24])([CH3:23])[CH3:21])=[O:26])=[N:4][CH:5]=[C:6]([N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2=[O:17])[CH:7]=1

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 902812293-Bromo-5-(1,3-dioxoisoindolin-2-yl)picolinaldehyde

Product 1

HCID 90281260(NZ,S)-N-[[3-bromo-5-(1,3-dioxoisoindol-2-yl)-2-pyridinyl]methylidene]-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Copper(II) sulfate (anhydrous, 5.8 g, 36.2 mmol) was added to a solution of 3-bromo-5-(1,3-dioxoisoindolin-2-yl)picolinaldehyde (30B, 6 g, 18 mmol) and (S)-2-methylpropane-2-sulfinamide (2.2 g, 18 mmol) in CH2Cl2 (60 mL). The reaction mixture was stirred at ambient temperature for 2 hours and then filtered and washed with CH2Cl2. The filtrate was concentrated and the residue was purified by silica gel chromatography eluting with EtOAc and methylene chloride to yield the title compound. MS (m/z) 433.87 [M+H]+.

Workup

  1. filtrationfiltered
  2. washwashed with CH2Cl2
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with EtOAc and methylene chloride

Sources & evidence

ORD record
ord-127895442d4441c89adbac399234af29
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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