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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
Notes
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Reaction equation

HRID 1098521 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6264e8b8a6e24a20a6b3e0c868bce4ba
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08143271B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes