Trifluoroacetic acid → HCID 59593271, compound

HRID 1367324Notes

Reaction equation

HRID 1367324 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-98ba4d738bc94fa6a298bb124946a674
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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