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Trifluoroacetic acid → 1-benzenesulfonyl-1H-indole-5-carboxylic acid hydroxyamide

HRID 84179
Notes
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Reaction equation

HRID 84179 reaction equation
[NH2:1][O:2]C1CCCCO1.[C:9]1([S:15]([N:18]2[C:26]3[C:21](=[CH:22][C:23]([C:27]([OH:29])=O)=[CH:24][CH:25]=3)[CH:20]=[CH:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C(O)(C(F)(F)F)=O>CN(C=O)C.CO>[OH:2][NH:1][C:27]([C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[N:18]([S:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:17])=[O:16])[CH:19]=[CH:20]2)=[O:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2724699PyBOPHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 109465411-Phenylsulfonylindole-5-carboxylic acid

Product 1

HCID 534645751-benzenesulfonyl-1H-indole-5-carboxylic acid hydroxyamide
Yield 52.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

NH2OTHP (0.08 g, 0.72 mmol) was added to a solution of 3 (0.18 g, 0.60 mmol), PyBOP (0.33 g, 0.63 mmol), and triethylamine (0.20 ml, 1.43 mmol) in DMF (1.5 mL). The reaction mixture was stirred at room temperature for 2 h before it was quenched with water and extracted with EtOAc (15 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (CH2Cl2:CH3OH=30:1:1% NH3(aq)) to give a white solid, which was treated with TFA (1.70 ml, 22.89 mmol) in the presence of CH3OH (31 mL). The reaction mixture was stirred overnight at room temperature before it was concentrated under reduced pressure to give a white residue. The residue was recrystallized with CH3OH to afford Compound 1 (0.10 g). 1H NMR (500 MHz, CD3OD): δ 6.80 (d, J=3.65 Hz, 1H), 7.49-7.52 (m, 2H), 7.59-7.62 (m, 1H), 7.68 (d, J=8.53 Hz, 1H), 7.75 (d, J=3.72 Hz, 1H), 7.93 (d, J=7.52 Hz, 2H), 7.94-7.97 (m, 1H), 8.04 (d, J=8.53 Hz, 1H); HRMS (EI) for C15H12N2O4S (M+): calcd, 316.0518. found, 316.0518.

Workup

  1. customwas quenched with water
  2. extractionextracted with EtOAc (15 mL×3)
  3. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (CH2Cl2:CH3OH=30:1:1% NH3(aq))
  6. customto give a white solid, which
  7. stirringThe reaction mixture was stirred overnight at room temperature before it
  8. concentrationwas concentrated under reduced pressure
  9. customto give a white residue
  10. customThe residue was recrystallized with CH3OH

Sources & evidence

ORD record
ord-f732c9da32ce419e95f414a1422a86c2
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846748B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes