Trifluoroacetic acid → HCID 58086713, compound

HRID 1098452Notes

Reaction equation

HRID 1098452 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([Cl:28])=[C:11]([CH:16](OC)[C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[C:12]([F:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[CH2:1]([O:8][C:9]1[C:10]([Cl:28])=[C:11]([C:12]([F:15])=[CH:13][CH:14]=1)[CH2:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58087042HCID 58087042, compound

Product 1

HCID 58086713HCID 58086713, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-[(3-Benzyloxy-2-chloro-6-fluoro-phenyl)-methoxy-methyl]-1H-pyrrolo[2,3-b]pyridine (P-1867, 0.1 g, 0.2 mmol), trifluoroacetic acid (0.6 mL, 8 mmol), and triethylsilane (0.3 mL, 2 mmol) in acetonitrile (10 mL) was refluxed for 2 hours. The mixture was concentrated and the residue was dissolved in ethyl acetate. The solution was washed with saturated sodium bicarbonate, brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with methanol in dichloromethane to provide compound as an off-white solid (P-1852, 62 mg, 70%). MS (ESI) [M+H+]+=367.16.

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with saturated sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of solvent
  7. customthe residue was purified by silica gel column chromatography
  8. washeluting with methanol in dichloromethane

Sources & evidence

ORD record
ord-ddc0458c772242d095a6cde59151d9af
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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