N,N-Dimethylformamide--water (1/1) → 6-Acetyl-5-trifluoromethyl-nicotinonitrile

HRID 545089ノート

反応式

HRID 545089 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.[CH3:15][N:16](C=O)C.O>[C-]#N.[C-]#N.[Zn+2].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:15]#[N:16])=[CH:7][N:6]=1)(=[O:10])[CH3:9]

参加物

6

反応物 2

HCID 21962138N,N-Dimethylformamide--water (1/1)HCID 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 3

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

反応条件

温度
120 °C

実験手順

Dissolve 1-(5-bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone (2.67 g, 0.01 mol) in anhydrous DMF/H2O (30.0:0.3 mL) and degas the resulting solution with N2 for 10 minutes. Add Zn(CN)2 (1.17 g, 0.01 mol), Pd2(dba)3 (229 mg, 2.5 mol %) and DPPF (270 mg, 5 mol %). Purge the mixture with N2 for another 10 minutes and heat at 120° C. under N2 atmosphere for 45 minutes. Cool the reaction mixture to room temperature, dilute with water, extract with EtOAc (3×75 mL) and dry (MgSO4). Filter the dried extract and concentrate under vacuum to afford the crude product, which is purified by column chromatography to afford the title product as a yellow solid.

後処理

  1. customdegas the resulting solution with N2 for 10 minutes
  2. customPurge the mixture with N2 for another 10 minutes
  3. temperatureCool the reaction mixture to room temperature
  4. additiondilute with water
  5. extractionextract with EtOAc (3×75 mL)
  6. dry with materialdry (MgSO4)
  7. filtrationFilter the dried
  8. extractionextract
  9. concentrationconcentrate under vacuum
  10. customto afford the crude product, which
  11. customis purified by column chromatography

出典と根拠

ORDレコード
ord-c72bae1c6ac94d2d8550f12b05f9a01b
出典データセット
uspto-grants-2011_05
特許番号
US07935702B2

反応ノート

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