Sodium Carbonate → 1-[2-(4-Hydroxymethyl-phenyl)-ethyl]-4-(5-methyl-pyridin-2-ylmethoxy)-1H-pyridin-2-one

HRID 564145ノート

反応式

HRID 564145 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][CH:19]=3)[C:12](=[O:26])[CH:11]=2)=[N:6][CH:7]=1.[C:27]([O-])([O-])=O.[Na+].[Na+].CB(O)O>O1CCOCC1>[OH:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][N:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([CH3:27])=[CH:7][N:6]=3)=[CH:11][C:12]2=[O:26])=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 139377Methylboronic AcidHCID 670073734-(5-Bromo-pyridin-2-ylmethoxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

生成物 1

HCID 670069761-[2-(4-Hydroxymethyl-phenyl)-ethyl]-4-(5-methyl-pyridin-2-ylmethoxy)-1H-pyridin-2-one

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To 300 mg (0.72 mmol) 4-(5-bromo-pyridin-2-ylmethoxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (example 12.1a) is added 25 mg (0.04 mmol) bis(triphenylphosphan)palladium(II)-chloride, 1.08 mL (2.17 mmol) 2 M aqueous Na2CO3-solution and a solution of 65 mg (1.08 mmol) methyl-boronic acid in 10 mL 1,4-dioxane/5 mL MeOH. The reaction mixture is refluxed for 48 h. The solvent is evaporated and the residue is dissolved in water/DCM. The layers are separated and the aqueous phase is extracted with DCM. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

後処理

  1. temperatureThe reaction mixture is refluxed for 48 h
  2. customThe solvent is evaporated
  3. dissolutionthe residue is dissolved in water/DCM
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted with DCM
  6. dry with materialThe combined organic phase is dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent is evaporated
  9. customThe residue is purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90)

出典と根拠

ORDレコード
ord-6a1e7c8f8dd5463cad1062dd26775417
出典データセット
uspto-grants-2011_11
特許番号
US08067590B2

反応ノート

読み込み中…