tert-Butylsulfinamide, (R)-(+)- → HCID 90200305, compound

HRID 1396328Notes

Reaction equation

HRID 1396328 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=O.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>C(Cl)Cl.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:9]=[C:6](/[CH:7]=[N:17]/[S@@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])[C:5]([F:10])=[N:4][CH:3]=1

Participants

6

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 454801925-Bromo-2-fluoro-3-pyridinecarboxaldehyde

Product 1

HCID 90200305HCID 90200305, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-bromo-2-fluoronicotinaldehyde (5 g, 24.51 mmol) and titanium (IV) ethoxide (15.42 ml, 73.5 mmol) in DCM (49.0 mL) was added (R)-2-methylpropane-2-sulfinamide (3.12 g, 25.7 mmol). The reaction mixture was then stirred at rt for 48 h. After 48 h, the reaction mixture was poured into brine at rt while rapidly stirring the mixture. The resulting suspension was filtered through a plug of CELITE®, and the filter cake was washed several times with DCM. The filtrate were separated, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give 7.6 g of crude product which was further purified using silica gel chromatography to yield the desired product (6.97 g, 93%) as an off white solid. MS (ESI) m/z: 330.8 (M+Na)+.

Workup

  1. waitAfter 48 h
  2. stirringwhile rapidly stirring the mixture
  3. filtrationThe resulting suspension was filtered through a plug of CELITE®
  4. washthe filter cake was washed several times with DCM
  5. customThe filtrate were separated
  6. washthe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give 7.6 g of crude product which
  11. customwas further purified

Sources & evidence

ORD record
ord-457b9afcc3e04403be88a09e58b47656
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

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