Trifluoroacetic acid → HCID 59803902, compound

HRID 250641Notes

Reaction equation

HRID 250641 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:27])=[C:11]([CH:15](OC)[C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH:12]=[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]([CH3:27])=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH2:15][C:16]1[C:24]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 598038763-[(3-benzyloxy-2-methyl-phenyl)-methoxy-methyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59803902HCID 59803902, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-[(3-benzyloxy-2-methyl-phenyl)-methoxy-methyl]-1H-pyrrolo[2,3-b]pyridine (625, 24 mg, 0.067 mmol), trifluoroacetic acid (1 mL, 13 mmol), and triethylsilane (2 mL, 12.5 mmol) in acetonitrile (10 mL) was refluxed for 4 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 washed with a mixture of ethyl ether and hexanes (1:1) to provide the compound as a yellow solid (P-1857, 17 mg, 75%). MS (ESI) [M+H+]+=329.24.

Workup

  1. temperaturewas refluxed for 4 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. washthe residue was washed with a mixture of ethyl ether and hexanes (1:1)

Sources & evidence

ORD record
ord-e4b5bb9297f44f50b2bfa4150c237475
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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