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Water → Ethyl 3-(5-(2-formyl-4-methoxyphenyl)picolinamido)propanoate

HRID 405174
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HRID 405174 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[N:6][CH:7]=1.[CH:18]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1B(O)O)=[O:19].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]>[CH:18]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[N:6][CH:7]=1)=[O:19]
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참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343652-Formyl-4-methoxybenzeneboronic acidHCID 62959749Ethyl 3-(5-bromopicolinamido)propanoate

생성물 1

HCID 86674255Ethyl 3-(5-(2-formyl-4-methoxyphenyl)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

Ethyl 3-(5-bromopicolinamido)propanoate (1.0 g, 3.3 mmol), (2-formyl-4-methoxyphenyl)boronic acid (896 mg, 5.0 mmol), Pd(dppf)Cl2 (364 mg, 0.5 mmol), and K2CO3 (918 mg, 6.6 mmol) were dissolved in 1,4-dioxane (20 mL) and water (5 mL) and heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

후처리

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

출처 및 근거

ORD 기록
ord-ce953ccbb1e8462b84bf0ec3d07e08f2
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748624B2

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