Water → 6-(1-Benzenesulfonyl-5-methylthio-1h-pyrrolo[2,3-b]pyridin-2-yl)nicotinic acid ethyl ester

HRID 1814113

反応式

HRID 1814113 の反応式
[C:1]1([S:7]([NH:10][C:11]2[C:16](I)=[CH:15][C:14]([S:18][CH3:19])=[CH:13][N:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([O:22][C:23]([C:25]1[CH:26]=[CH:27][C:28]([C:31]#[C:32][Si](C)(C)C)=[N:29][CH:30]=1)=[O:24])[CH3:21].C([O-])(=O)C.[K+].O>O1CCOCC1>[CH2:20]([O:22][C:23](=[O:24])[C:25]1[CH:26]=[CH:27][C:28]([C:31]2[N:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[C:11]3=[N:12][CH:13]=[C:14]([S:18][CH3:19])[CH:15]=[C:16]3[CH:32]=2)=[N:29][CH:30]=1)[CH3:21]

参加物

6

反応物 4

HCID 962WaterHCID 517044Potassium AcetateHCID 154868512-Benzenesulfonylamino-3-iodo-5-methylthiopyridineHCID 225043975-Ethoxycarbonyl-2-trimethylsilylethynylpyridine

生成物 1

HCID 684447396-(1-Benzenesulfonyl-5-methylthio-1h-pyrrolo[2,3-b]pyridin-2-yl)nicotinic acid ethyl ester収率 98.5%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-benzenesulfonylamino-5-methylthio-3-iodo-pyridine (100 mg) in 1,4-dioxane (2.5 ml), 5-ethoxycarbonyl-2-trimethylsilylethynylpyridine (185 mg), bistriphenylphosphine palladium dichloride (9 mg), cuprous iodide (5 mg) and potassium acetate (37 mg) were added successively and the mixture was stirred in a sealed tube at 100° C. for 15 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate=2:1) to obtain 110 mg of the desired product as an orange oil.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was separated

出典と根拠

ORDレコード
ord-0f1fd7e7c0f54fbc91234c3ff00dc5b1
出典データセット
uspto-grants-2005_04
特許番号
US06875770B2

関連ノート

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