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

HRID 385595ノート

反応式

HRID 385595 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-399de85177a64d5d9c02a3609fd8c7eb
出典データセット
uspto-grants-2013_02
特許番号
US08367831B2

反応ノート

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