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Potassium Carbonate → Methyl 3-phenylpicolinate

HRID 1099194
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HRID 1099194 반응식
FC(F)(F)S(O[C:7]1[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>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>[C:25]1([C:7]2[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 11066008Methyl 3-(trifluoromethylsulfonyloxy)-pyridine-2-carboxylate

생성물 1

HCID 11063767Methyl 3-phenylpicolinate수율 79.7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 1140
Toluene
용매

실험 절차

To a solution of methyl 3-{[(trifluoromethyl)sulfonyl]oxy}pyridine-2-carboxylate (148.6 g, 521 mmol) in anhydrous toluene (550 ml) were added potassium carbonate (148.6 g), tetrakis(triphenylphosphine)palladium(0) (6 g), and phenyl boronic acid (70 g, 574 mmol). The reaction was equipped with a mechanical stirring apparatus and heated to reflux for 2 h. The reaction suspension was filtered through a bed of celite and washed with EtOAc. The filtrate was concentrated in vacuo and purified via flash chromatography (silica, 20% EtOAc/hexanes isocratic) to provide methyl 3-phenylpyridine-2-carboxylate (88.5 g).

후처리

  1. customThe reaction was equipped with a mechanical stirring apparatus
  2. temperatureheated
  3. temperatureto reflux for 2 h
  4. filtrationThe reaction suspension was filtered through a bed of celite
  5. washwashed with EtOAc
  6. concentrationThe filtrate was concentrated in vacuo
  7. custompurified via flash chromatography (silica, 20% EtOAc/hexanes isocratic)

출처 및 근거

ORD 기록
ord-3171a615d8104a19b9c234f5bf490b67
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08143405B2

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