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

HRID 405236노트

반응식

HRID 405236 반응식
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH3:10].CC1(C)C(C)(C)OB([C:33]2[CH:34]=[CH:35][C:36]([C:39]([NH:41][CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[O:40])=[N:37][CH:38]=2)O1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.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:8][C:6]1[CH:5]=[CH:4][C:3]([CH:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH3:10])=[C:2]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([NH:41][CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[O:40])=[N:37][CH:38]=2)[CH:7]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoateHCID 71060075N-(1-(2-bromo-4-chlorophenyl)ethyl)-4'-fluoro-[1,1'-biphenyl]-4-amine

생성물 1

HCID 71060007Ethyl 3-(5-(5-chloro-2-(1-((4'-fluoro-[1,1'-biphenyl]-4-yl)amino)ethyl)phenyl)picolinamido)propanoate

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6228Dimethylformamide용매

실험 절차

N-(1-(2-bromo-4-chlorophenyl)ethyl)-4′-fluoro-[1,1′-biphenyl]-4-amine (138 mg, 0.34 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (142 mg, 0.41 mmol), Pd(dppf)Cl2 (37 mg, 0.05 mmol), and K2CO3 (108 g, 0.78 mmol) were dissolved in wet DMF (3 mL) and water (4 mL) and heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, filtered through CELITE and the filtrate was diluted with EtOAc, washed with water and sat. aqueous NaHCO3. The organic layer was dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

후처리

  1. filtrationfiltered through CELITE
  2. additionthe filtrate was diluted with EtOAc
  3. washwashed with water and sat. aqueous NaHCO3
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified via column chromatography

출처 및 근거

ORD 기록
ord-2acd82919088448981d50d61705f75cd
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748624B2

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