Cesium carbonate → (6'-Methyl-2,3'-bipyridin-5-yl)methanol

HRID 82469ノート

反応式

HRID 82469 の反応式
Br[C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N:16]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[CH:18][C:17]=1[CH3:31]>C1COCC1.ClCCl>[CH3:31][C:17]1[N:16]=[CH:21][C:20]([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[CH:6][N:7]=2)=[CH:19][CH:18]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 64212496-Bromo-3-pyridinemethanolHCID 164142722-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

生成物 1

HCID 67031985(6'-Methyl-2,3'-bipyridin-5-yl)methanol

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

To a solution of (6-bromo-pyridin-3-yl)-methanol (0.614 g, 3.27 mmol) in 10 mL of THF under an atmosphere of nitrogen was added cesium carbonate (3.27 mL, 2 N aqueous, 6.53 mmol), 2-picoline-5-boronic acid pinacol ester (0.477 g, 2.18 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II), 1:1 complex with dichloromethane (0.178 g, 0.218 mmol). The reaction was heated at 85° C. for 1 h, cooled to rt, and diluted with dichloromethane. The organic solution was washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The aqueous fraction was concentrated in vacuo, triturated 3× with 20% methanol in dichloromethane, and collected via filtration. The combined solids were purified via silica gel chromatography, eluting with 100% ethyl acetate to provide (6′-methyl-2,3′-bipyridin-5-yl)methanol that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 201.1 for [M+H]+.

後処理

  1. temperaturecooled to rt
  2. washThe organic solution was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationThe aqueous fraction was concentrated in vacuo
  7. customtriturated 3× with 20% methanol in dichloromethane
  8. filtrationcollected via filtration
  9. customThe combined solids were purified via silica gel chromatography
  10. washeluting with 100% ethyl acetate

出典と根拠

ORDレコード
ord-73427a7aac264955874c53cdb4953e94
出典データセット
uspto-grants-2014_09
特許番号
US08846702B2

反応ノート

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