Triphenyl Phosphate → 4-cyano-3-(2'-cyano-biphenyl-4-yl)-1-methyl-5-trifluoromethyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 1865114

반응식

HRID 1865114 반응식
[C:1]([C:3]1[C:4]([C:18]2[CH:23]=[CH:22][C:21](OS(C(F)(F)F)(=O)=O)=[CH:20][CH:19]=2)=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]([CH3:12])[C:7]=1[C:8]([F:11])([F:10])[F:9])#[N:2].[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1B(O)O)#[N:33].C1(OP(OC2C=CC=CC=2)(OC2C=CC=CC=2)=O)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH2:16]([O:15][C:13]([C:5]1[N:6]([CH3:12])[C:7]([C:8]([F:9])([F:10])[F:11])=[C:3]([C:1]#[N:2])[C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[C:32]#[N:33])=[CH:20][CH:19]=1)=[O:14])[CH3:17]

참가 물질

7

반응물 4

HCID 8289Triphenyl PhosphateHCID 62657Potassium Phosphate, TribasicHCID 27346102-Cyanophenylboronic acidHCID 86611446Ethyl 4-cyano-1-methyl-5-(trifluoromethyl)-3-{4-[(trifluoromethyl)sulfonyloxy]phenyl}pyrrole-2-carboxylate

생성물 1

HCID 690203034-cyano-3-(2'-cyano-biphenyl-4-yl)-1-methyl-5-trifluoromethyl-1H-pyrrole-2-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

Prepare the title compound in a manner analogous to the procedure described in Scheme IIIa. For example, place ethyl 4-cyano-1-methyl-5-(trifluoromethyl)-3-{4-[(trifluoromethyl)sulfonyloxy]phenyl}pyrrole-2-carboxylate (11.0 mmol, prepared in example E-277), 2-cyano-phenyl boronic acid (1.5 mmol), palladium (II) acetate (0.12 mmol), triphenylphosphate (0.24 mmol), and tribasic potassium phosphate (3.6 mmol) in a round bottom flask and add dioxane. Heat reaction to reflux for 18 hours, remove the heat and wash with water while extracting with ethyl acetate. Dry organics with sodium sulfate, filter, and concentrate in vacuo. Purify the residue via radial chromatography eluting with methylene chloride, ethyl acetate and hexane to provide the title compound.

후처리

  1. temperatureHeat
  2. customreaction
  3. temperatureto reflux for 18 hours
  4. customremove the
  5. temperatureheat
  6. washwash with water
  7. extractionwhile extracting with ethyl acetate
  8. filtrationDry organics with sodium sulfate, filter
  9. concentrationconcentrate in vacuo
  10. customPurify the residue via radial chromatography
  11. washeluting with methylene chloride, ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-ffa9f4a52e6b4dd1b4dda9fa526e2679
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625932B2

연결된 노트

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