3-(Trifluoromethyl)aniline → 4-Bromo-N-(3-(trifluoromethyl)phenyl)picolinamide

HRID 338726

Reaktionsgleichung

Reaktionsgleichung von HRID 338726
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[F:42][C:43]([F:52])([F:51])[C:44]1[CH:45]=[C:46]([CH:48]=[CH:49][CH:50]=1)[NH2:47]>CN(C)C=O.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:47][C:46]2[CH:48]=[CH:49][CH:50]=[C:44]([C:43]([F:42])([F:51])[F:52])[CH:45]=2)=[O:10])[CH:3]=1

Komponenten

7

Edukt 4

HCID 73753-(Trifluoromethyl)anilineHCID 79724-MethylmorpholineHCID 7351504-Bromopyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 866958504-Bromo-N-(3-(trifluoromethyl)phenyl)picolinamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 4-bromo-pyridine-2-carboxylic acid (1.00 g, 5.00 mmol) in dimethylformamide (5 mL) was added 1-methylmorpholine (1.1 mL, 10 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate (HATU) (2.37 g, 6.23 mmol). The mixture became an orange solution after 10 minutes. 3-Trifluoromethylaniline (0.5 mL, 5.5 mmol) was added and the solution was stirred at room temperature for 21 hours. The dimethylformamide was evaporated in vacuo and the residue was triturated with water. The resulting solid was filtered and washed twice with water and then vacuum dried at 40° C. to give a crude residue. Chromatography on silica gel (40 g), sample applied in dichloromethane and eluted with hexanes:ethyl acetate (1:1) gave the title compound (1.306 g, 76%).

Aufarbeitung

  1. customafter 10 minutes
  2. customThe dimethylformamide was evaporated in vacuo
  3. customthe residue was triturated with water
  4. filtrationThe resulting solid was filtered
  5. washwashed twice with water
  6. customvacuum dried at 40° C.
  7. customto give a crude residue
  8. washeluted with hexanes:ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8bb99e47b35d46048bda3a10485f3bd9
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889870B2

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