Trifluoroacetic acid → HCID 59593271, compound

HRID 1952072Notes

Reaction equation

HRID 1952072 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)O)=[CH:4][CH:3]=1.BrC1N=CC(C(OC)C2C3C(=NC=CC=3)NC=2)=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86610503HCID 86610503, compoundHCID 86610504HCID 86610504, compound

Product 1

HCID 59593271HCID 59593271, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (6-bromo-pyridin-3-yl)-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (89, 1 g, 0.003 mol) and 3-[(6-bromo-pyridin-3-yl)-methoxy-methyl]-1H-pyrrolo[2,3-b]pyridine (90, 2 g, 0.006 mol), triethylsilane (1 mL, 0.006 mol), and trifluoroacetic acid (0.5 mL, 0.006 mol) in acetonitrile (25 mL) was refluxed for 2 hours. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate and water. The organic layer was collected, washed with saturated sodium bicarbonate, brine, and dried over sodium sulfate. After removal of the solvent, the residue was purified with silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as an off-white solid (91, 0.75 g, 60%). MS (ESI) [M+H+]+=288.06, 290.00.

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customThe organic layer was collected
  5. washwashed with saturated sodium bicarbonate, brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removal of the solvent
  8. customthe residue was purified with silica gel column chromatography
  9. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-663bd0cd4490489384ef5eee167f16a1
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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