Aniline → 4-Bromo-pyridine-2-carboxylic acid phenylamide

HRID 338700

反応式

HRID 338700 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.[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C)C=O>[C:43]1([NH:42][C:8]([C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][N:5]=2)=[O:10])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

参加物

6

反応物 4

HCID 6115AnilineHCID 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 866958264-Bromo-pyridine-2-carboxylic acid phenylamide収率 71.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 4-bromo-pyridine-2-carboxylic acid (1.00 g, 5.00 mmol) in dimethylformamide (10 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. Aniline (0.5 mL, 5.5 mmol) was added and the solution was stirred at room temperature for 66 hours. The dimethylformamide was evaporated in vacuo and the residue was partitioned between water and ethyl acetate. The separated water layer was extracted with ethyl acetate. The combined ethyl acetate extract was washed with water and saturated sodium bicarbonate. The organic layer was dried (MgSO4), filtered and evaporated to crude 2. Chromatography on silica gel (40 g) applied in dichloromethane and eluted with hexanes:ethyl acetate (1:1) gave the title compound (0.986 g, 71%).

後処理

  1. customafter 10 minutes
  2. customThe dimethylformamide was evaporated in vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. extractionThe separated water layer was extracted with ethyl acetate
  5. extractionThe combined ethyl acetate extract
  6. washwas washed with water and saturated sodium bicarbonate
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated to crude 2
  10. washeluted with hexanes:ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-5ff8ad58779c434bace6846b494b7950
出典データセット
uspto-grants-2014_11
特許番号
US08889870B2

関連ノート

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