Trifluoroacetic acid → HCID 29553240, compound

HRID 509940Notes

Reaction equation

HRID 509940 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[F:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[F:9])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 67970o-FluorobenzaldehydeHCID 706222-Amino-5-bromopyridine

Product 1

HCID 29553240HCID 29553240, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

In a round bottom flask, 5-bromo-pyridin-2-ylamine (38, 4.05 g g, 23.4 mmol) was combined with 70.0 mL of acetonitrile, 2-fluoro-benzaldehyde (39, 2.45 mL, 23.4 mmol), triethylsilane (20.0 mL, 125 mmol) and trifluoroacetic acid (10.0 mL, 130 mmol). The reaction was stirred at 80° C. for 3 hours. The reaction was poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20-60% ethyl acetate in hexane. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (40, 5.0 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material was purified by silica gel column chromatography
  6. washeluting with 20-60% ethyl acetate in hexane
  7. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-ed72b866d8ff418e8a639feb8428dbd2
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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