Dimethylformamide → 4-(2-tert-butyl-1H-imidazol-5-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine

HRID 44915

반응식

HRID 44915 반응식
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:6]=12)=O.C[N:23]([CH:25]=O)C.[C:27]([O-])(=O)[C:28]([CH3:31])(C)[CH3:29].[Cs+].C([O-])(=O)C.[NH4+:39]>O>[C:28]([C:25]1[NH:23][C:3]([C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:6]=23)=[CH:2][N:39]=1)([CH3:31])([CH3:29])[CH3:27]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 517165Ammonium AcetateHCID 583616Cesium pivalateHCID 574775702-chloro-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)ethanone

생성물 1

HCID 574775694-(2-tert-butyl-1H-imidazol-5-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine수율 52%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 2-chloro-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)ethanone (prepared, e.g., as in Ex. 50, Step 1) (0.054 g, 0.00017 mol) in DMF (1.8 mL, 0.023 mol) was added cesium pivalate (0.0389 g, 0.000166 mol) and the reaction was stirred at room temperature for 16 hours. Ammonium acetate (0.45 g, 0.0058 mol) was added, and the reaction was heated in the microwave to 170° C. for 5 minutes. Water was added and the product was extracted with MTBE. The combined organic extracts were dried over sodium sulfate, then filtered and concentrated. The crude residue was purified by flash column chromatography (2.5% MeOH/DCM) to yield 4-(2-tert-butyl-1H-imidazol-5-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine (32 mg, 52%). 1H NMR (400 MHz, CDCl3): 8.31 (d, 1H), 7.50 (s, 1H), 7.40 (d, 1H), 7.37 (d, 1H), 6.94 (d, 1H), 5.69 (s, 2H), 3.52 (dd, 2H), 1.46 (s, 9H), 0.90 (dd, 2H), −0.08 (s, 9H); MS(ES): 371 (M+1).

후처리

  1. temperaturethe reaction was heated in the microwave to 170° C. for 5 minutes
  2. extractionthe product was extracted with MTBE
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography (2.5% MeOH/DCM)

출처 및 근거

ORD 기록
ord-89b3030e1aee43b69129a8b520f25b85
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541425B2

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