5-Chloro-2-fluoro-4-iodopyridine → 4-(((5-chloro-4-iodopyridin-2-yl)amino)methyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 1521973Notes

Reaction equation

HRID 1521973 reaction equation
[Cl:1][C:2]1[C:3]([I:9])=[CH:4][C:5](F)=[N:6][CH:7]=1.[NH2:10][CH2:11][C:12]1([C:18]#[N:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CS(C)=O>[Cl:1][C:2]1[C:3]([I:9])=[CH:4][C:5]([NH:19][CH2:18][C:12]2([C:11]#[N:10])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 218653365-Chloro-2-fluoro-4-iodopyridineHCID 552854014-(Aminomethyl)oxane-4-carbonitrile

Product 1

HCID 904120784-(((5-chloro-4-iodopyridin-2-yl)amino)methyl)tetrahydro-2H-pyran-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-chloro-2-fluoro-4-iodopyridine (1 g, 3.88 mmol) and 4-(aminomethyl)tetrahydro-2H-pyran-4-carbonitrile (1.634 g, 11.65 mmol) in 4 mL of dimethylsulfoxide was heated at 100° C. for 8 hours. The mixture was quenched with 100 mL of ice-cold water and was extracted with ethyl acetate (50 mL×2). The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 20% ethyl acetate in hexane) afforded the title compound.

Workup

  1. customThe mixture was quenched with 100 mL of ice-cold water
  2. extractionwas extracted with ethyl acetate (50 mL×2)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (silica gel, 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5ecc5686a7ee48a3b533b157d3dc9242
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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