Water → 6-((4-Chlorobenzyl)amino)-2-fluoronicotinaldehyde

HRID 1256740Notes

Reaction equation

HRID 1256740 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[N:13]=[C:12]([F:14])[C:11]([CH2:15][OH:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>O1CCCC1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[N:13]=[C:12]([F:14])[C:11]([CH:15]=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 59593272[6-(4-Chloro-benzylamino)-2-fluoro-pyridin-3-yl]-methanol

Product 1

HCID 595932856-((4-Chlorobenzyl)amino)-2-fluoronicotinaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [6-(4-Chloro-benzylamino)-2-fluoro-pyridin-3-yl]-methanol (63, 1.0 g, 3.7 mmol) in tetrahydrofuran (50.0 mL) was added Dess-Martin periodinane (1.75 g, 4.12 mmol). The reaction was stirred at room temperature for 10 minutes, then poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a white solid (64, 0.67 g, 68.0%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane
  7. customto give a white solid (64, 0.67 g, 68.0%)

Sources & evidence

ORD record
ord-2734787a2f9b4180a552365f845ed1ba
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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