Dimethylformamide → 6-Acetyl-5-trifluoromethyl-nicotinonitrile

HRID 545075ノート

反応式

HRID 545075 の反応式
Br[C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[Cl-].[NH4+].[OH-].[NH4+].[CH3:19][N:20](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:8]([C:5]1[C:4]([C:11]([F:14])([F:13])[F:12])=[CH:3][C:2]([C:19]#[N:20])=[CH:7][N:6]=1)(=[O:10])[CH3:9]

参加物

9

反応物 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 586455621-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

生成物 1

HCID 671902526-Acetyl-5-trifluoromethyl-nicotinonitrile

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒2 回

実験手順

Heat a solution of 1-(5-bromo-3-trifluoromethyl-pyridin-2-yl)-ethanone (268 mg, 1.0 mmol), zinc cyanide (75 mg, 0.63 mmol), pd2(dba)3 (30 mg), and DPPF (35 mg) in DMF (3 mL) and water (0.03 mL), under a nitrogen atmosphere, at 120° C. for 1 hour. Cool the reaction to 0° C. and add a solution of saturated ammonium chloride solution (2 mL), water (2 mL) and concentrated ammonium hydroxide (0.5 mL) and stir for 1 hour. Extract the mixture with ethyl acetate (3×20 mL) and wash the combined organics with brine (50 mL). Dry the organic extract over MgSO4 and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with a 9:1 mixture of hexane:ether to give the title compound.

後処理

  1. temperatureCool
  2. customthe reaction to 0° C.
  3. extractionExtract the mixture with ethyl acetate (3×20 mL)
  4. washwash the combined organics with brine (50 mL)
  5. customDry the
  6. extractionorganic extract over MgSO4
  7. customremove the solvent under reduced pressure
  8. customPurify the residue by flash chromatography
  9. washeluting with a 9:1 mixture of hexane

出典と根拠

ORDレコード
ord-e208a2f3aa8c4ae9a315254d1fb6cdb4
出典データセット
uspto-grants-2011_05
特許番号
US07935702B2

反応ノート

読み込み中…