5-Bromo-3-pyridinecarboxaldehyde → N-((5-bromopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide

HRID 1897823Notes

Reaction equation

HRID 1897823 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.[CH3:10][C:11]([S:14]([NH2:16])=[O:15])([CH3:13])[CH3:12]>C1(C)C=CC=CC=1.[Cl-].[Na+].O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[N:16][S:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 66745079N-((5-bromopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 5-bromo-pyridine-3-carbaldehyde (2 g, 10.75 mmol), 2-methylpropane-2-sulfinamide (1.434 g, 11.83 mmol) and titanium(IV) isopropoxide (12.60 ml, 43.0 mmol) in toluene (53.8 ml) was stirred for 16 h at room temperature. Brine was added and the precipitate removed and washed with AcOEt. The organic layer was dried over MgSO4, filtered and concentrated to give the title compound that was used as is for the next step. LC-MS (M+1) 291.0.

Workup

  1. customthe precipitate removed
  2. washwashed with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-77267cc8a10949439a0ac554ef006c9e
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

Loading…