Trifluoroacetic acid → HCID 86653329, compound

HRID 510005Notes

Reaction equation

HRID 510005 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[C:11]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=3)[C:4]=12)#[CH:2].[F:20][C:21]([F:31])([F:30])[C:22]1[N:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][CH:23]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>O.C(#N)C>[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[C:11]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([NH:19][CH2:28][C:25]4[CH:26]=[N:27][C:22]([C:21]([F:31])([F:20])[F:30])=[CH:23][CH:24]=4)=[N:17][CH:18]=3)[C:4]=12)#[CH:2]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 58259176HCID 58259176, compound

Product 1

HCID 86653329HCID 86653329, compoundYield 10.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

In a round bottom flask, 5-(4-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine (164, 0.055 g, 0.22 mmol) was combined with 6-trifluoromethyl-pyridine-3-carbaldehyde (160, 50.4 mg, 0.288 mmol), 0.682 mL of acetonitrile, trifluoroacetic acid (0.0853 mL, 1.11 mmol), and triethylsilane (0.212 mL, 1.33 mmol) and the reaction heated to reflux for 3 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, then dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with methanol and dichloromethane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (P-1717, 9.3 mg). MS (ESI) [M+H+]+=408.5.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel column chromatography
  9. washeluting with methanol and dichloromethane
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ad06212478774fa3afeb491aa9f701c5
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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