Potassium Carbonate → HCID 89782826, 화합물

HRID 58056

반응식

HRID 58056 반응식
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][NH:5][C:6]=1[CH3:7].Br[CH2:10][C:11]1([CH3:15])[CH2:14][O:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:1][C:2]1[C:3]([CH3:8])=[N:4][N:5]([CH2:10][C:11]2([CH3:15])[CH2:14][O:13][CH2:12]2)[C:6]=1[CH3:7]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 769374-bromo-3,5-dimethyl-1H-pyrazoleHCID 144860Oxetane, 3-(bromomethyl)-3-methyl-

생성물 1

HCID 89782826HCID 89782826, 화합물수율 49.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

To a 4 mL vial equipped with a magnetic stir bar were added 4-bromo-3,5-dimethyl-1H-pyrazole (150 mg, 0.857 mmol), 3-(bromomethyl)-3-methyloxetane (283 mg, 1.714 mmol), K2CO3 (355 mg, 2.57 mmol), and acetonitrile (2 mL). The contents of the vial were stirred to give a white suspension. The vial was heated in a sand bath to 70° C. for 24 hours, and the reaction mixture was subsequently partitioned between water (15 mL) and ethyl acetate (20 mL). The layers were separated and the aqueous layer was back-extracted with ethyl acetate (20 mL). The combined organic layers were concentrated and the residue was purified via flash chromatography (4 g column) eluting with a gradient of 0-70% EtOAc in heptanes. The pure fractions were combined and concentrated to give the title compound as a clear liquid (110 mg, 49.5%).

후처리

  1. customTo a 4 mL vial equipped with a magnetic stir bar
  2. customto give a white suspension
  3. customthe reaction mixture was subsequently partitioned between water (15 mL) and ethyl acetate (20 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was back-extracted with ethyl acetate (20 mL)
  6. concentrationThe combined organic layers were concentrated
  7. customthe residue was purified via flash chromatography (4 g column)
  8. washeluting with a gradient of 0-70% EtOAc in heptanes
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ad38f0e623d747e39deab37cc0c76e07
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434743B2

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