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

HRID 1948278ノート

反応式

HRID 1948278 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7854Propionitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-efde362751ba4da9a7303547faa98ee0
出典データセット
uspto-grants-2013_03
特許番号
US08399493B2

反応ノート

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