Potassium Carbonate → Ethyl 3-(5-(3-chloro-2-(((2',4'-dichloro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405190노트

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HRID 405190 반응식
Br[C:2]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([Cl:28])[C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])=[CH:8][CH:7]=1.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[CH:39][C:40]([C:43]([NH:45][CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[O:44])=[N:41][CH:42]=2)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CCOC(C)=O.[Na+].[Cl-].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.Cl[Pd]Cl.[Fe+2]>[Cl:28][C:20]1[C:3]([CH2:4][NH:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])=[CH:10][CH:11]=2)=[C:2]([C:37]2[CH:38]=[CH:39][C:40]([C:43]([NH:45][CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[O:44])=[N:41][CH:42]=2)[CH:23]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:21]=1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoateHCID 86674262N-(2-bromo-6-chloro-4-(trifluoromethyl)benzyl)-2',4'-dichloro-[1,1'-biphenyl]-4-amine

생성물 1

HCID 86674264Ethyl 3-(5-(3-chloro-2-(((2',4'-dichloro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 5234Sodium Chloride용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

N-(2-bromo-6-chloro-4-(trifluoromethyl)benzyl)-2′,4′-dichloro-[1,1′-biphenyl]-4-amine (4.5 g, 8.8 mmol) and ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (3.1 g, 8.8 mmol), Pd(dppf)Cl2 (321 mg, 0.4 mmol), and 2 M K2CO3 (aq) (8.8 mL, 17.6 mmol) were dissolved in 1,4-dioxane (35 mL) and heated to 80° C. After 1 h the reaction was cooled to room temperature diluted with EtOAc and 4M aqueous NaCl, and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organics were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

후처리

  1. temperatureAfter 1 h the reaction was cooled to room temperature
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified via column chromatography

출처 및 근거

ORD 기록
ord-904a29be2f904a329d513cce73f35540
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748624B2

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