Sodium Iodide → 1-((6-Iodopyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one

HRID 1948278Notes

Reaction equation

HRID 1948278 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:12]=[CH:11][C:10]2=[O:23])=[CH:4][CH:3]=1.C[Si](Cl)(C)C.[Na+].[I-:30]>C(#N)CC>[I:30][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:12]=[CH:11][C:10]2=[O:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 862293191-((6-chloropyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one

Product 1

HCID 862293681-((6-Iodopyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

According to Scheme 33 Step 1: 1-((6-Chloropyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (2.54 mmol, 0.83 g), trimethylsilyl chloride (3.3 mmol, 0.42 mL) and NaI (7.60 mmol, 1.14 g) in propionitrile (20 mL) were heated at 140° C. for 20 minutes under microwave irradiation conditions. Then the suspension was filtered off and the solid obtained was partitioned between CH2Cl2/water. The aqueous layer was extracted several times with CH2Cl2; the organic layers were combined, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was treated with Et2O giving an 1-((6-iodopyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (600 mg, 61%) as a pale grey solid.

Workup

  1. filtrationThen the suspension was filtered off
  2. customthe solid obtained
  3. customwas partitioned between CH2Cl2/water
  4. extractionThe aqueous layer was extracted several times with CH2Cl2
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was evaporated under reduced pressure
  7. additionThe residue was treated with Et2O giving an 1-((6-iodopyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (600 mg, 61%) as a pale grey solid

Sources & evidence

ORD record
ord-efde362751ba4da9a7303547faa98ee0
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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