5-bromo-2,4-dichloropyridine → HCID 90204301, 화합물

HRID 1480186노트

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HRID 1480186 반응식
Br[C:2]1[C:3]([Cl:9])=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.C([Mg]Cl)(C)C.[O:15]1[CH2:18][C:17](=[O:19])[CH2:16]1>C1COCC1.C(OCC)(=O)C>[Cl:9][C:3]1[CH:4]=[C:5]([Cl:8])[N:6]=[CH:7][C:2]=1[C:17]1([OH:19])[CH2:18][O:15][CH2:16]1

참가 물질

6

반응물 3

HCID 121751335-bromo-2,4-dichloropyridineHCID 150242543-OxetanoneHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 90204301HCID 90204301, 화합물수율 72%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
-15 °C

실험 절차

To a solution of 5-bromo-2,4-dichloropyridine (CAN 849937-96-8, 15 g, 66.1 mmol) in dry THF (300 ml) cooled down to −15° C. under an argon atmosphere was added isopropyl magnesium chloride, lithium chloride complex (53.4 ml, 69.4 mmol) and the mixture was stirred at −15° C. for 1 hour. Then oxetan-3-one (5.24 g, 72.7 mmol) was added neat to the reaction mixture cooled at −15° C., reaction mixture was stirred and let to warm up to room temperature overnight. Reaction was quenched by addition of water and stirred for 5 minutes. Reaction was diluted with ethyl acetate and was transferred into a separatory funnel. The organic phase was extracted with a saturated aqueous solution of ammonium chloride and the organic phase was collected. The aqueous phase was back-extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (10.5 mg, 72%). MS (ESI, m/z): 220.4 (M+H+)

후처리

  1. temperaturecooled at −15° C.
  2. customreaction mixture
  3. stirringwas stirred
  4. temperatureto warm up to room temperature overnight
  5. customReaction
  6. customwas quenched by addition of water
  7. stirringstirred for 5 minutes
  8. customReaction
  9. customwas transferred into a separatory funnel
  10. extractionThe organic phase was extracted with a saturated aqueous solution of ammonium chloride
  11. customthe organic phase was collected
  12. extractionThe aqueous phase was back-extracted with ethyl acetate
  13. dry with materialThe combined organic phases were dried over sodium sulfate
  14. customevaporated down to dryness
  15. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

출처 및 근거

ORD 기록
ord-d112e010cb6e4d47b6544c84d4c6668f
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409866B2

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