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Cesium carbonate → Methyl 2-chloro-6-phenylpyridine-4-carboxylate

HRID 1096962
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HRID 1096962 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10](=O)([O-])[O-].[Cs+].[Cs+].[Cl:16][C:17]1[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[CH:20]=[C:19](Cl)[N:18]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Cl:16][C:17]1[CH:22]=[C:21]([C:23]([O:25][CH3:10])=[O:24])[CH:20]=[C:19]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 948302,6-Dichloroisonicotinic acid

생성물 1

HCID 53485792Methyl 2-chloro-6-phenylpyridine-4-carboxylate

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran
용매

실험 절차

Phenylboronic acid (326 mg), PdCl2(PPh3)2 (84 mg) and cesium carbonate (3.9 g) were added in that order to a THF (10 mL) solution of 2,6-dichloropyridine-4-carboxylic acid (500 mg), and stirred under heat with refluxing for 1.5 hours. The reaction liquid was filtered through Celite, concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain a crude product of the title compound as a yellow oil. Not purified, this was used in the next step.

후처리

  1. temperatureunder heat
  2. temperaturewith refluxing for 1.5 hours
  3. customThe reaction liquid
  4. filtrationwas filtered through Celite
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-267175a88285425692536c261fc80bcb
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08138197B2

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