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

HRID 82469노트

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HRID 82469 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매

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온도
85 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-73427a7aac264955874c53cdb4953e94
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846702B2

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