2-Pyridinecarboxaldehyde → (1-Methyl-1H-imidazol-5-yl)(pyridin-2-yl)methanol

HRID 520841

반응식

HRID 520841 반응식
C([Mg]Cl)(C)C.[Cl-].[Li+].Br[C:9]1[N:13]([CH3:14])[CH:12]=[N:11][CH:10]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]=[O:22]>C1COCC1>[CH3:14][N:13]1[C:9]([CH:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=2)[OH:22])=[CH:10][N:11]=[CH:12]1

참가 물질

5

반응물 3

HCID 142732-PyridinecarboxaldehydeHCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 178461733HCID 178461733, 화합물

생성물 1

HCID 86715604(1-Methyl-1H-imidazol-5-yl)(pyridin-2-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

A solution of isopropylmagnesium chloride/lithium chloride complex (1.3 M in THF, 19.5 mL, 25.35 mmol) was added dropwise by syringe to a solution of 5-bromo-1-methyl-1H-imidazole (4.12 g, 25.58 mmol) in dry THF (130 mL) at 0° C. After 15 minutes, the Grignard solution was added via cannulation to a solution of picolinaldehyde (2.0 ml, 20.93 mmol) in dry THF (55 mL) at 0° C. The reaction mixture was stirred for 5 minutes at 0° C., then warmed to room temperature for 1 hour. The reaction mixture was then cooled in an ice bath and quenched with saturated aqueous ammonium chloride. The mixture was partitioned between brine and ethyl acetate. The separated aqueous phase was further extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-5% MeOH-DCM) to provide the title compound as a white solid.

후처리

  1. temperaturewarmed to room temperature for 1 hour
  2. temperatureThe reaction mixture was then cooled in an ice bath
  3. customquenched with saturated aqueous ammonium chloride
  4. customThe mixture was partitioned between brine and ethyl acetate
  5. extractionThe separated aqueous phase was further extracted with ethyl acetate
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash column chromatography (silica gel, 0-5% MeOH-DCM)

출처 및 근거

ORD 기록
ord-ce3ec1c8d3974353a11504b793e9359d
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328095B2

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