Hydrochloric Acid → HCID 59589379、化合物

HRID 577137ノート

反応式

HRID 577137 の反応式
Br[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([Cl:13])[CH:5]=[CH:4][N:3]=1.[CH:14]([Zn]C(C)C)([CH3:16])[CH3:15].O.Cl>O1CCOCC1>[Cl:13][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH:14]([CH3:16])[CH3:15])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 59589350Ethyl 2-bromo-4-chloropyridine-3-carboxylateHCID 178461828HCID 178461828、化合物

生成物 1

HCID 59589379HCID 59589379、化合物収率 50%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
40 °C

実験手順

Ethyl 2-bromo-4-chloropyridine-3-carboxylate (1 g, 3.78 mmol) was dissolved in anhydrous dioxane (30 mL). A solution of diisopropyl zinc (4.5 mL, 4.54 mmol, 1.0 M in toluene) was added dropwise, followed with (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (44 mg, 60 μmol). The mixture was heated at 40° C. overnight, and water followed with 1 N HCl was added. The reaction mixture was extracted 3 times with ethyl acetate, and the combined organic phases were washed with brine and dried over sodium sulfate. After evaporation, the residue was dissolved in DCM and purified on silica gel using 0-15% hexane/ethyl acetate to afford ethyl 4-chloro-2-(propan-2-yl)pyridine-3-carboxylate (428 mg, 50% yield).

後処理

  1. additionwas added
  2. extractionThe reaction mixture was extracted 3 times with ethyl acetate
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation
  6. dissolutionthe residue was dissolved in DCM
  7. custompurified on silica gel using 0-15% hexane/ethyl acetate

出典と根拠

ORDレコード
ord-366c4809872e4b2c85742a7d6302a590
出典データセット
uspto-grants-2015_05
特許番号
US09040538B2

反応ノート

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