Tert-Butanesulfinamide → HCID 66893740, compound

HRID 1487560Notes

Reaction equation

HRID 1487560 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=O)=[N:6][CH:7]=1.[CH3:10][C:11]([S:14]([NH2:16])=[O:15])([CH3:13])[CH3:12]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[N:16][S:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 66893740HCID 66893740, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-Bromo-pyridine-2-carbaldehyde (2.0 g, 10.753 mmol) in CH2Cl2 (20 mL) and 2-Methyl-propane-2-sulfinic acid amide (2.602 g, 21.505 mmol) is added CuSO4 (5.589 g, 21.505 mmol) at room temperature. Resulting reaction mixture is stirred at room temperature for 3 hours. Reaction mixture is filter through celite. Diluted with water and extracted with CH2Cl2. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by combi-flash chromatography using 5% ethyl acetate in hexane to afford the title compound (2.5 g): 1H-NMR (400 MHz, DMSO-d6) δ: 1.19 (s, 9H), 8.03 (d, J=8.52 Hz, 1H), 8.25-8.27 (dd, J=2.32 Hz, J=8.32 Hz, 1H), 8.44 (s, 1H), 8.90 (d, J=1.84 Hz, 1H). LC-MS (m/z): [M+H]=291.1.

Workup

  1. customResulting
  2. customreaction mixture
  3. customReaction mixture
  4. filtrationis filter through celite
  5. additionDiluted with water
  6. extractionextracted with CH2Cl2
  7. dry with materialOrganic layer is dried over sodium sulphate, solvent
  8. customis evaporated in vacuo
  9. custompurified by combi-flash chromatography

Sources & evidence

ORD record
ord-e13c1eda5b314f249615386c9283f5bc
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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