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Potassium Carbonate → Methyl 3-phenylpicolinate

HRID 1099194
ノート
印刷プレビュー

反応式

HRID 1099194 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

HCID 11063767Methyl 3-phenylpicolinate収率 79.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 1140
Toluene
溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3171a615d8104a19b9c234f5bf490b67
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08143405B2

反応ノート

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