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Ethanol → 4-(6-Cyano-5-methoxy-pyridin-2-yl)-benzoic acid ethyl ester

HRID 983414
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인쇄 미리보기

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HRID 983414 반응식
Br[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][CH3:11])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].B(O)(O)[C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=1.[CH2:30](O)[CH3:31]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:30]([O:27][C:25](=[O:26])[C:22]1[CH:23]=[CH:24][C:19]([C:2]2[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([C:8]#[N:9])[N:7]=2)=[CH:20][CH:21]=1)[CH3:31]
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참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 225607406-Bromo-3-methoxypicolinonitrile

생성물 1

HCID 693568724-(6-Cyano-5-methoxy-pyridin-2-yl)-benzoic acid ethyl ester

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

A solution of 6-bromo-3-methoxy-pyridine-2-carbonitrile from Example 13c in toluene is treated with 2 M Na2CO3 (aqueous), 4-carboxylphenylboronic acid (1 equiv.), ethanol and catalytic (Ph3P)4Pd) and is heated at 80° C. for 18 h. The reaction mixture is evaporated and the residue is dissolved in ethanol with 4 N HCl in dioxane and heated at reflux for 18 h. The reaction mixture is evaporated, the residue taken into ethyl acetate, washed with 5% Na2CO3 (aqueous), dried over MgSO4 and evaporated to give 4-(6-cyano-5-methoxy-pyridin-2-yl)-benzoic acid ethyl ester.

후처리

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in ethanol with 4 N HCl in dioxane
  3. temperatureheated
  4. temperatureat reflux for 18 h
  5. customThe reaction mixture is evaporated
  6. washwashed with 5% Na2CO3 (aqueous)
  7. dry with materialdried over MgSO4
  8. customevaporated

출처 및 근거

ORD 기록
ord-3df59f582e864af8874b5c75ebad279c
출처 데이터셋
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06864267B2

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