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Water → Ethyl 3-(5-(4,5-difluoro-2-(hydroxymethyl)phenyl)picolinamido)propanoate

HRID 405206
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HRID 405206 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][OH:11].CC1(C)C(C)(C)OB([C:20]2[CH:21]=[CH:22][C:23]([C:26]([NH:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[N:24][CH:25]=2)O1.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]>[F:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([NH:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[N:24][CH:25]=2)=[C:3]([CH2:10][OH:11])[CH:4]=1
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참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 57518297(2-Bromo-4,5-difluorophenyl)methanolHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate

생성물 1

HCID 71060054Ethyl 3-(5-(4,5-difluoro-2-(hydroxymethyl)phenyl)picolinamido)propanoate

시약·촉매·용매 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

실험 절차

(2-bromo-4,5-difluorophenyl)methanol (2.8 g, 12.5 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (4.8 g, 13.7 mmol), Pd(dppf)Cl2 (1.4 g, 1.9 mmol), and K2CO3 (3.4 g, 24.9 mmol) were dissolved in 1,4-dioxane (28 mL) and water (15 mL) and the resulting mixture was heated to 85° C. After 2 h the resulting mixture was diluted with EtOAc and the layers were separated. The organic layer was dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

후처리

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

출처 및 근거

ORD 기록
ord-5e370d896edc455ab4047138d7c959f9
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748624B2

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