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

HRID 338726ノート

反応式

HRID 338726 の反応式
[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

参加物

7

反応物 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)

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-8bb99e47b35d46048bda3a10485f3bd9
出典データセット
uspto-grants-2014_11
特許番号
US08889870B2

反応ノート

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