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

HRID 391339Notes

Reaction equation

HRID 391339 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-8ce28787e70649d4b69c3478aab8531b
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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