Trifluoroacetic acid → HCID 59593326, compound

HRID 1024162Notes

Reaction equation

HRID 1024162 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]([F:20])([F:19])[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH2:15][C:14]2[CH:13]=[CH:12][C:11]([C:10]([F:9])([F:19])[F:20])=[CH:18][CH:17]=2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 679964-(Trifluoromethyl)benzaldehydeHCID 706222-Amino-5-bromopyridine

Product 1

HCID 59593326HCID 59593326, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a round bottom flask fitted with stirrer and reflux condenser was added 2-amino-5-bromopyridine (15, 1.73 mol, 300 g) and p-trifluoromethylbenzaldehyde (16, 1.723 mol, 300 g) to a solution of trifluoroacetic acid (400 mL), triethylsilane (825 mL) and acetonitrile (7500 mL). The reaction was heated to reflux overnight (24 hours). Solvents were removed and the residue was poured into aqueous K2CO3 and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated. The crude compound was crystallized with diethyl ether/hexane to afford compound 17, 420 g (73.6%) as off white solid. MS (ESI) [M+H+]+=331.1 and 333.1 (1:1 ratio).

Workup

  1. customInto a round bottom flask fitted with stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction was heated
  4. temperatureto reflux overnight (24 hours)
  5. customSolvents were removed
  6. additionthe residue was poured into aqueous K2CO3
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe crude compound was crystallized with diethyl ether/hexane

Sources & evidence

ORD record
ord-ad7cfac8e4f94aa98f40f72a429486b3
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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