Water → 1-benzenesulfonyl-2-(5-methylfuran-2-yl)-5-methylthio-1H-pyrrolo[2,3-b]pyridine

HRID 1814074노트

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HRID 1814074 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][C:24]([CH3:27])=[CH:25][CH:26]=1)#[CH:21].C(N(CC)CC)C.O>O1CCOCC1>[C:1]1([S:7]([N:10]2[C:11]3=[N:12][CH:13]=[C:14]([S:18][CH3:19])[CH:15]=[C:16]3[CH:21]=[C:20]2[C:22]2[O:23][C:24]([CH3:27])=[CH:25][CH:26]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 124280182-Ethynyl-5-methylfuranHCID 154868512-Benzenesulfonylamino-3-iodo-5-methylthiopyridine

생성물 1

HCID 225044451-benzenesulfonyl-2-(5-methylfuran-2-yl)-5-methylthio-1H-pyrrolo[2,3-b]pyridine수율 88%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

To a solution of 2-benzenesulfonylamino-5-methylthio-3-iodopyridine (203 mg) in 1,4-dioxane (5 ml), 2-ethynyl-5-methylfuran (160 mg), bistriphenylphosphine palladium dichloride (18 mg), cuprous iodide (10 mg) and triethylamine (75 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 preparative thin-layer chromatography (hexane:ethyl acetate=5:1) to obtain 169 mg of the desired products 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-ad9cb97c4b504fd09fdc9b2e09e6c507
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875770B2

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