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

HRID 405132노트

반응식

HRID 405132 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[C:17]2[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=2)=[C:4]([F:33])[CH:3]=1.[Cl:34][C:35]1[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:36]=1B(O)O.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.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:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:5]2[CH:6]=[CH:7][C:2]([C:38]3[CH:37]=[CH:36][C:35]([Cl:34])=[CH:40][C:39]=3[Cl:41])=[CH:3][C:4]=2[F:33])=[C:11]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=2)[CH:12]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 71059944Ethyl 3-(5-(2-(((4-bromo-2-fluorophenyl)amino)methyl)-5-chlorophenyl)picolinamido)propanoate

생성물 1

HCID 71059882Ethyl 3-(5-(5-chloro-2-(((2',4'-dichloro-3-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

시약·촉매·용매 3

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

실험 절차

Ethyl 3-(5-(2-(((4-bromo-2-fluorophenyl)amino)methyl)-5-chlorophenyl)picolinamido)propanoate (138 mg, 0.26 mmol), (2,4-dichlorophenyl)boronic acid (57 mg, 0.30 mmol), Pd(dppf)Cl2 (21 mg, 0.03 mmol), and K2CO3 (71 mg, 0.52 mmol) were dissolved in 1,4-dioxane (1.0 mL) and water (0.25 mL) and the resulting mixture was heated to 80° C. After 3 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

후처리

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

출처 및 근거

ORD 기록
ord-213489b3530b4c1f8b34fe19769cda88
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748624B2

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