Sodium 1-Methyl 3-Sulfinopropionate → HCID 89526185, compound

HRID 2278344Notes

Reaction equation

HRID 2278344 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[N:6]=[CH:5]2.[CH3:17][O:18][C:19](=[O:25])[CH2:20][CH2:21][S:22]([O-:24])=[O:23].[Na+]>[Cu]I>[CH3:15][CH:14]([S:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([S:22]([CH2:21][CH2:20][C:19]([O:18][CH3:17])=[O:25])(=[O:24])=[O:23])=[CH:10][CH:9]=2)[CH:5]=[N:6]1)(=[O:13])=[O:12])[CH3:16]

Participants

4

Reactant 2

HCID 23665669Sodium 1-Methyl 3-SulfinopropionateHCID 89526146HCID 89526146, compound

Product 1

HCID 89526185HCID 89526185, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
110 °C

Procedure

5-bromo-1-(propan-2-ylsulfonyl)-1H-indazole (0.85 g, 2.79 mmol), sodium 3-methoxy-3-oxopropane-1-sulfinate (2.42 g, 13.9 mmol) and CuI (2.66 g, 13.9 mmol) were charged in a sealable microwave flask. The flask was closed and degassed twice, after which dry DMSO (3.0 mL) was added and the reaction mixture degassed before being heated at 110° C. in an oil bath overnight. The reaction mixture was cooled and diluted with ethyl acetate (40 mL), and then filtered on a silica gel pad and eluted with ethyl acetate. The organic phases were concentrated under reduced pressure. The crude was purified on silica gel eluting with hexanes and ethyl acetate, then with DCM and methanol to afford the title compound.

Workup

  1. customThe flask was closed
  2. customdegassed twice
  3. additionafter which dry DMSO (3.0 mL) was added
  4. customthe reaction mixture degassed
  5. temperatureThe reaction mixture was cooled
  6. additiondiluted with ethyl acetate (40 mL)
  7. filtrationfiltered on a silica gel pad
  8. washeluted with ethyl acetate
  9. concentrationThe organic phases were concentrated under reduced pressure
  10. customThe crude was purified on silica gel eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-7db4abf56e1b47a0978f518de01e02c8
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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