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

HRID 2407451Notes

Reaction equation

HRID 2407451 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-8976f4378e88476cb2170f4d099ef0ce
Source dataset
uspto-grants-2014_08
Patent number
US08809545B2

Reaction notes

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