Hydrochloric Acid → HCID 59589379, 화합물

HRID 577137노트

반응식

HRID 577137 반응식
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]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 59589350Ethyl 2-bromo-4-chloropyridine-3-carboxylateHCID 178461828HCID 178461828, 화합물

생성물 1

HCID 59589379HCID 59589379, 화합물수율 50%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-366c4809872e4b2c85742a7d6302a590
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040538B2

반응 노트

불러오는 중…