Water → 1H-Pyrrolo[2,3-b]pyridine, 2-(2-furanyl)-5-(methylthio)-1-(phenylsulfonyl)-

HRID 1432205

反応式

HRID 1432205 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.[C:20]([C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)#[CH:21].C(N(CC)CC)C.O>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[O:23]1[CH:24]=[CH:25][CH:26]=[C:22]1[C:20]1[N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:11]2=[N:12][CH:13]=[C:14]([S:18][CH3:19])[CH:15]=[C:16]2[CH:21]=1

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 140409Furan, 2-ethynyl-HCID 154868512-Benzenesulfonylamino-3-iodo-5-methylthiopyridine

生成物 1

HCID 154868521H-Pyrrolo[2,3-b]pyridine, 2-(2-furanyl)-5-(methylthio)-1-(phenylsulfonyl)-収率 85%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-benzenesulfonylamino-3-iodo-5-methylthiopyridine (1.60 g) in dioxane (40 ml), 2-ethynylfuran (725 mg), bis(triphenylphosphine) palladium chloride (138 mg), copper(I) iodide (75 mg) and triethylamine (598 mg) were added successively and the mixture was stirred in a sealed tube at 60° C. for 1 hour. After cooling, the reaction solution was poured into water, extracted with dichloromethane, dried over, anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 1.24 g (85%) of the desired product as a brown oil.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane
  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-a12745ff9f1c4a2f8d983518ef770b87
出典データセット
uspto-grants-2009_11
特許番号
US07612070B2

関連ノート

読み込み中…