Trifluoroacetic acid → HCID 59803902, compound

HRID 253400Notes

Reaction equation

HRID 253400 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 (60, 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-9008e8a9e98f4ce38ef4538e8193fe4c
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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