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Trifluoroacetic acid → 2-[3-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,4-difluoro-phenoxy]-ethanol

HRID 1098521
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HRID 1098521 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[C:15]([O:20][CH2:21][CH2:22][O:23]C4CCCCO4)[C:14]=3[F:30])O)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:13]3[C:14]([F:30])=[C:15]([CH:16]=[CH:17][C:18]=3[F:19])[O:20][CH2:21][CH2:22][OH:23])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58087553(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,6-difluoro-3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl-methanol

생성물 1

HCID 580862892-[3-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-2,4-difluoro-phenoxy]-ethanol수율 35.2%

시약·촉매·용매 1

HCID 6342Acetonitrile
용매

실험 절차

To (5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,6-difluoro-3-[2-(tetrahydro -pyran-2-yloxy)-ethoxy]-phenyl-methanol (542, 0.22 g, 0.46 mmol) in acetonitrile (6.0 mL) were added trifluoroacetic acid (0.14 mL, 1.8 mmol) and triethylsilane (0.29 mL, 1.8 mmol). The reaction was stirred at room temperature overnight. The filtrate was concentrated and purified by silica gel column chromatography eluting with 35% ethyl acetate in hexane to give the compound as a white solid (P-1392, 62 mg, 35%). MS (M+H+)+=383.1, 385.1.

후처리

  1. concentrationThe filtrate was concentrated
  2. custompurified by silica gel column chromatography
  3. washeluting with 35% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-6264e8b8a6e24a20a6b3e0c868bce4ba
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08143271B2

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