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Trifluoroacetic acid → HCID 86703316, compound

HRID 2409999
Notes
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Reaction equation

HRID 2409999 reaction equation
[C:1](/[CH:3]=[CH:4]/[C:5]1[N:10]=[C:9]([CH2:11][C:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[N:14](C(OC(C)(C)C)=O)[C:13]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:8]=[CH:7][CH:6]=1)#[N:2].FC(F)(F)C(O)=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C.ClCCl>[CH3:22][O:21][C:17]1[CH:16]=[C:15]2[C:20]([C:12]([CH2:11][C:9]3[N:10]=[C:5](/[CH:4]=[CH:3]/[C:1]#[N:2])[CH:6]=[CH:7][CH:8]=3)=[C:13]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[NH:14]2)=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86703315HCID 86703315, compound

Product 1

HCID 86703316HCID 86703316, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 21877088
Acetonitrile methylene chloride
Solvent

Procedure

To a solution of tert-butyl 3-[6-((E)-2-cyanovinyl)pyridin-2-ylmethyl]-6-methoxy-2-phenyl-1H-indole-1-carboxylate (100 mg) in acetonitrile/dichloromethane (1 mL/1 mL) was added trifluoroacetic acid (1 mL) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture were added ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (68.7 mg). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 4.40 (2H, s), 6.60 (1H, d, J=16.1 Hz), 6.76 (1H, dd, J=2.1, 8.7 Hz), 6.91 (1H, d, J=2.1 Hz), 7.07-7.16 (2H, m), 7.32-7.49 (5H, m), 7.50-7.63 (3H, m), 8.05 (1H, br s).

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0092d38833c5492d9a6dba00d6d75ed9
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08815903B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes