Potassium Carbonate → 6-(2,4-Difluorophenoxy)-3-iodo-4-methyl-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one

HRID 2114557ノート

反応式

HRID 2114557 の反応式
[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[C:10](=[O:11])[N:9]([CH3:12])[C:8]2[CH:13]=[N:14][N:15](COCC[Si](C)(C)C)[C:7]=2[CH:6]=1.[I:29]Cl.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.ClCCl>[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[C:10](=[O:11])[N:9]([CH3:12])[C:8]2[C:13]([I:29])=[N:14][NH:15][C:7]=2[CH:6]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 24640Iodine chloride2 回HCID 598128336-(2,4-Difluorophenoxy)-4-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one

生成物 1

HCID 1784815796-(2,4-Difluorophenoxy)-3-iodo-4-methyl-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one収率 10.3%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 6-(2,4-difluorophenoxy)-4-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one (118 mg, 0.289 mmol) in chloroform (25 mL) was added iodine monochloride (141 mg, 3 eq) followed by potassium carbonate (200 mg, 5 eq) and the resulting mixture was heated under reflux with stirring (in the dark) for 24 hours. Additional iodine monochloride (large excess) was added and the resulting solution was stirred under reflux for another 16 hours. The reaction mixture was cooled to room temperature and diluted with dichloromethane, and washed 2× with an aqueous solution of Na2S2O3(aq) followed by brine. The organic layer was dried over magnesium sulfate, filtered and concentrated to give the crude product as an oil (97 mg). Purification by Preparative Thin Layer Chromatography eluting with 60% ethyl acetate in hexanes gave the title compound as an off-white powder (12 mg, (M+H)+=462).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux
  3. stirringthe resulting solution was stirred
  4. temperatureunder reflux for another 16 hours
  5. washwashed 2× with an aqueous solution of Na2S2O3(aq)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product as an oil (97 mg)
  10. customPurification by Preparative Thin Layer Chromatography
  11. washeluting with 60% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-dcc26051cedf4be09ce7dca90883b5f4
出典データセット
uspto-grants-2008_10
特許番号
US07435731B2

反応ノート

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