Trifluoroacetic acid → HCID 86703323, compound

HRID 2410008Notes

Reaction equation

HRID 2410008 reaction equation
O[CH:2]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[NH:15][C:14]=1[C:24]1[CH:25]=[N:26][CH:27]=[N:28][CH:29]=1)[C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:23][O:22][C:18]1[CH:17]=[C:16]2[C:21]([C:13]([CH2:2][C:3]3[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=3)=[C:14]([C:24]3[CH:25]=[N:26][CH:27]=[N:28][CH:29]=3)[NH:15]2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052Triethylsilane2×HCID 86703322HCID 86703322, compound

Product 1

HCID 86703323HCID 86703323, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of methyl 6-[hydroxyl(6-methoxy-2-pyrimidin-5-yl-1H-indol-3-yl)methyl]pyridine-2-carboxylate (828 mg) in dichloromethane (21.2 mL) was added triethylsilane (1.35 mL) under ice-cooling. Then trifluoroacetic acid (0.649 mL) was added dropwise thereto, and the mixture was stirred under ice-cooling for 30 minutes and then at room temperature for 1 hour. Triethylsilane (1.35 mL) and trifluoroacetic acid (0.649 mL) were added thereto, and the mixture was stirred at room temperature for additional 5 hours. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was 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: methanol-ethyl acetate) to obtain the title compound (468 mg). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 4.03 (3H, s), 4.48 (2H, s), 6.80 (1H, dd, J=2.3, 8.8 Hz), 6.92 (1H, d, J=2.3 Hz), 7.23-7.28 (1H, m), 7.37 (1H, d, J=8.8 Hz), 7.64-7.71 (1H, m), 7.94-8.00 (1H, m), 8.16 (1H, br s), 9.04 (2H, s), 9.17 (1H, s). ESI-MS (m/z): 375 (M+H)+

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. stirringthe mixture was stirred at room temperature for additional 5 hours
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluting solvent: methanol-ethyl acetate)

Sources & evidence

ORD record
ord-b5d8e549c515445cad07f16aa33cca20
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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