Diisopropylethylamine → 1H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

HRID 1098506노트

반응식

HRID 1098506 반응식
[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Si:20](OS(C(F)(F)F)(=O)=O)([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22]>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 111599156-Bromo-7-azaindole

생성물 1

HCID 580876901H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
50 °C

실험 절차

6-bromo-1H-pyrrolo[2,3-b]pyridine (587, 275 mg, 1.39 mmol) was dissolved in 4 mL of dry dioxane. DIEA (3 equiv) and TIPS-OTf (2.5 equiv) were added and the reaction was stirred at 50° C. overnight. The reaction was then diluted with 20 mL of ethyl acetate and washed 2 times with 10 mL NaHCO3 (aq., 5%) and once with 10 mL brine. The organic fraction was dried over MgSO4, evaporated and diluted with 5.5 mL of dry toluene 10 mg bromide per 0.2 mL of solution) to use directly in the next reaction step.

후처리

  1. washwashed 2 times with 10 mL NaHCO3 (aq., 5%)
  2. dry with materialThe organic fraction was dried over MgSO4
  3. customevaporated
  4. additiondiluted with 5.5 mL of dry toluene 10 mg bromide per 0.2 mL of solution)
  5. customto use directly in the next reaction step

출처 및 근거

ORD 기록
ord-26db3e664336498ab8c6b133e465834f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143271B2

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