Trifluoroacetic acid → HCID 975849, compound

HRID 2387280Notes

Reaction equation

HRID 2387280 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH2:14][C:13]2[CH:16]=[CH:17][C:10]([Cl:9])=[CH:11][CH:12]=2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 77264-ChlorobenzaldehydeHCID 12052TriethylsilaneHCID 706222-Amino-5-bromopyridine

Product 1

HCID 975849HCID 975849, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2-amino-5-bromopyridine (54, 6.10 g, 0.0352 mol) in toluene (90.0 mL) were added 4-chlorobenzaldehyde (55, 5.00 g, 0.0356 mol), trifluoroacetic acid (8.0 mL, 0.10 mol) and triethylsilane (16.5 mL, 0.103 mol). The reaction was heated to reflux for 48 hours. The reaction was concentrated, poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The crude residue was crystallized with ethyl acetate to give compound (56, 6.8 g, 65.4%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 48 hours
  3. concentrationThe reaction was concentrated
  4. additionpoured into aqueous potassium carbonate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude residue was crystallized with ethyl acetate
  10. customto give compound (56, 6.8 g, 65.4%)

Sources & evidence

ORD record
ord-5f76101a089e402c92aadf33e31a1ab5
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

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