p-Toluenesulfonic acid → HCID 66914340, compound

HRID 2104595Notes

Reaction equation

HRID 2104595 reaction equation
[C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29][O:30]C(OC)OC.[C:36]1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])[O-].C[O-].[Na+]>CO>[CH3:36][O:8][C:7]([O:30][CH3:29])([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:25]([F:28])([F:26])[F:27]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 10942334Sodium MethoxideHCID 11360909Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanoneHCID 21585117Orthoformate2×

Product 1

HCID 66914340HCID 66914340, compoundYield 813.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone (0.210 g, 0.56 mmol) in MeOH (5 mL) is refluxed with trimethylorthoformate (0.12 mL, 1.12 mmol) and para-toluenesulfonic acid (0.005 g). After 5 h, additional orthoformate (0.20 mL) is added. After 3 h more, more orthoformate (0.20 mL) is added. After refluxing overnight, the reaction is cooled and treated with NaOMe in methanol (0.5 mL). After 10 min of stirring, the reaction is concentrated and the residue chromatographed eluting with 5:95 ethyl acetate:hexanes to afford the title compound as a white solid (0.100 g). MS (ESI) m/z 424; HRMS: calcd for C25H20F3NO2+H, 424.15244; found (ESI, [M+H]+), 424.1519.

Workup

  1. waitAfter 3 h more
  2. temperatureAfter refluxing overnight
  3. temperaturethe reaction is cooled
  4. concentrationthe reaction is concentrated
  5. customthe residue chromatographed
  6. washeluting with 5:95 ethyl acetate

Sources & evidence

ORD record
ord-daf870e75383467292a3eaf1ef4535ac
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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