Trifluoroacetic acid → (6-Bromo-pyridazin-3-yl)-(4-chloro-benzyl)-amine

HRID 1754710Notes

Reaction equation

HRID 1754710 reaction equation
[Br:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C.O>[Br:1][C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:14][C:13]2[CH:16]=[CH:17][C:10]([Cl:9])=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 77264-ChlorobenzaldehydeHCID 12052TriethylsilaneHCID 27947796-Bromopyridazin-3-amine

Product 1

HCID 57619288(6-Bromo-pyridazin-3-yl)-(4-chloro-benzyl)-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 6-bromo-pyridazin-3-ylamine (521, 0.85 g, 0.0049 mol) in acetonitrile (30.0 mL) were added 4-chlorobenzaldehyde (40, 0.82 g, 0.0058 mol), triethylsilane (4.0 mL, 0.025 mol) and trifluoroacetic acid (2.0 mL, 0.026 mol). The reaction was heated to reflux for 4 hours, then poured into water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and washed with ethyl acetate to give a white solid (522, 1.0 g). MS (ESI) [M+H+]+=298.3, 300.2.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. washwashed with ethyl acetate
  9. customto give a white solid (522, 1.0 g)

Sources & evidence

ORD record
ord-58b818027b27447ab74acdd446f76410
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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