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

HRID 1432205

반응식

HRID 1432205 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a12745ff9f1c4a2f8d983518ef770b87
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612070B2

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