Iodine → Methyl 6-formylpyridine-3-carboxylate

HRID 30451

Reaction equation

HRID 30451 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][CH:5]=1.II.IC(C)(C)C.FC(F)(F)C(O)=[O:22].[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:22])=[N:6][CH:5]=1

Participants

8

Reactant 6

HCID 807IodineHCID 6422Trifluoroacetic acidHCID 112062-Iodo-2-methylpropaneHCID 24477Sodium ThiosulfateHCID 231548Methyl 6-methylnicotinateHCID 516892Sodium Bicarbonate

Product 1

HCID 586269Methyl 6-formylpyridine-3-carboxylateYield 46.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 6-methyl nicotinic acid methyl ester (1.00 g, 6.62 mmol), iodine (1.68 g, 6.62 mmol), 2-iodo-2-methylpropane (0.478.g, 2.60 mmol) and trifluoroacetic acid (2.26 g, 19.8 mmol) in anhydrous DMSO was heated for 3 h at 160° C. The reaction mixture was cooled to room temperature (rt) and treated with 1 N aq. Na2S2O3 (50 mL). The reaction mixture was adjusted to pH 10 with 1 N aq. NaHCO3. The reaction mixture was extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated. Chromatography of the residue (SiO2; 0-3% EtOH:DCM) gave the title compound as a solid (0.506 g, 46%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (3×100 mL)
  2. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-38fdc4b8d6644238b6c81a8e61c3a852
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Linked notes

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