Potassium Carbonate → HCID 57974935, 화합물

HRID 1865110노트

반응식

HRID 1865110 반응식
[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]

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2734379(Pyridin-4-yl)boronic acidHCID 57974728HCID 57974728, 화합물

생성물 1

HCID 57974935HCID 57974935, 화합물

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e38f9dfee0d145f686af2d6a7b27098f
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625932B2

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