Cesium carbonate → [5-(Furan-2-yl)pyridin-3-yl]methanol

HRID 1510716노트

반응식

HRID 1510716 반응식
Br[C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1B(O)O.[Cl-].[Li+].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1

참가 물질

8

반응물 5

HCID 10796Cesium carbonateHCID 433294Lithium ChlorideHCID 2734357Furan-2-boronic acidHCID 2784733(5-Bromo-3-pyridinyl)methanolHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

생성물 1

HCID 24729849[5-(Furan-2-yl)pyridin-3-yl]methanol수율 41.9%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 0.10 g of (5-bromopyridin-3-yl)methanol in 5 mL of dioxane, 72 mg of 2-furanboronic acid, 67 mg of lithium chloride, 0.51 g of cesium carbonate, 5.4 mg of palladium acetate and 20 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl were added at room temperature, and the mixture was heated under reflux for 1 hour 30 minutes under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and the solvent was then distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=95:5 to 90:10 to obtain 39 mg of (5-(2-furyl)pyridin-3-yl)methanol as a yellow oily substance.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour 30 minutes under a nitrogen atmosphere
  3. distillationthe solvent was then distilled off under reduced pressure
  4. customThe resultant residue was purified by flash silica gel column chromatography
  5. washelution with chloroform

출처 및 근거

ORD 기록
ord-15b215dd7bb84305ac38ec7c26bda913
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211908B2

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