Triethylamine → 4-Chloro-2-ethyl-3-iodo-pyridine

HRID 1529208Notes

Reaction equation

HRID 1529208 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH2:6]([C:8]1[C:13]([I:14])=[C:12](O)[CH:11]=[CH:10][N:9]=1)[CH3:7].CCN(CC)CC>CC#N>[Cl:3][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:6][CH3:7])[C:13]=1[I:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178437639HCID 178437639, compound

Product 1

HCID 582353314-Chloro-2-ethyl-3-iodo-pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 165.1 g (1.08 mol) POCl3 in 100 mL CH3CN is added dropwise to a solution of 27.1 g (108 mmol) 2-ethyl-3-iodo-pyridin-4-ol in 150 mL CH3CN at RT. Then Et3N (21.9 g, 216 mmol) is added slowly over 20 min before the reaction mixture is heated to 60° C. for 3 h. The reaction mixture is evaporated in vaccuo to afford an oil. This crude oil is poured into the crushed ice, and the aqueous phase is extracted with petroleum ether/EtOAc (3×, 200 mL; 10:1). The organic phase is collected, dried over anhydrous Na2SO4. The solvent is removed in vacuo to afford desired product. Yield: 22.0 g (76%).

Workup

  1. customThe reaction mixture is evaporated in vaccuo
  2. customto afford an oil
  3. extractionthe aqueous phase is extracted with petroleum ether/EtOAc (3×, 200 mL; 10:1)
  4. customThe organic phase is collected
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-d53561fd0dd348ee96fc9ea2d0cba529
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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