Potassium Carbonate → HCID 57974935、化合物

HRID 1865110ノート

反応式

HRID 1865110 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:29])[C:8]([CH2:27][CH3:28])=[C:9]([C:25]#[N:26])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14](OS(C(F)(F)F)(=O)=O)=[CH:13][CH:12]=1)=[O:5])[CH3:2].[N:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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].O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:29])[C:8]([CH2:27][CH3:28])=[C:9]([C:25]#[N:26])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:33]2[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=2)=[CH:13][CH:12]=1)=[O:5])[CH3:2]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2734379(Pyridin-4-yl)boronic acidHCID 57974728HCID 57974728、化合物

生成物 1

HCID 57974935HCID 57974935、化合物

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

Add 4-cyano-5-ethyl-1-methyl-3-(4-trifluoromethanesulfonyloxy-phenyl)-1H-pyrrole-2-carboxylic acid ethyl ester (0.204 g, 0.474 mmol, prepared in example E-97a or E-97b), 4-pyridyl boronic acid (0.116 g, 0.948 mmol), Pd2(dba)3 (13.02 mg, 0.01422 mmol), triphenyl phosphine (14.92 mg, 0.0569 mmol), 2M aqueous potassium carbonate (2 mL, 4.0 mmol) in 3 ml of dioxane, and heat to reflux with stirring. After 2.5 hours, cool the reaction mixture and pour into water. Extract the quenched reaction with ethyl acetate. Combine the organic extracts, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with 1:1 ethyl acetate:hexanes to ethyl acetate to provide the title compound. Mass spectrum (m/e) 360.1 (M+1).

後処理

  1. temperatureheat
  2. temperatureto reflux
  3. temperaturecool the reaction mixture
  4. extractionExtract
  5. customthe quenched reaction with ethyl acetate
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. customPurify the residue by flash chromatography
  10. washeluting with 1:1 ethyl acetate

出典と根拠

ORDレコード
ord-e38f9dfee0d145f686af2d6a7b27098f
出典データセット
uspto-grants-2009_12
特許番号
US07625932B2

反応ノート

読み込み中…