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1-(Trimethylsilyl)prop-1-yne → 5-Bromo-3,4-dimethyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1626006
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HRID 1626006 반응식
[Br:1][C:2]1[C:3]([CH3:10])=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.C([O-])(=O)C.[K+].[Cl-].[Li+].[CH3:18][Si:19]([CH3:24])([CH3:23])[C:20]#[C:21][CH3:22]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]2[C:21]([CH3:22])=[C:20]([Si:19]([CH3:24])([CH3:23])[CH3:18])[NH:8][C:5]2=[N:6][CH:7]=1
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참가 물질

7

반응물 4

HCID 803631-(Trimethylsilyl)prop-1-yneHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 401518975-Bromo-3-iodo-4-methylpyridin-2-amine

생성물 1

HCID 670776815-Bromo-3,4-dimethyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

The compound obtained in step 1 of Example 36 (1.8 g) was dissolved in N,N-dimethylformamide (40 ml), and potassium acetate (1.7 g) and lithium chloride (0.3 g) were added. After replacing the atmosphere in the system with nitrogen, palladium acetate (0.13 g) and 1-trimethylsilyl-1-propyne (4.3 ml) were added and the mixture was stirred at 90° C. for three days. The reaction solution was cooled to room temperature and then N,N-dimethylformamide was distilled off. The resulting residue was diluted with ethyl acetate and then washed with brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to give the crude title compound (2.4 g).

후처리

  1. additionwere added
  2. temperatureThe reaction solution was cooled to room temperature
  3. distillationN,N-dimethylformamide was distilled off
  4. additionThe resulting residue was diluted with ethyl acetate
  5. washwashed with brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-fb74b887dfaf48ffb0bb0e3d14084ed4
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785438B2

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