Water → 2,2-Difluoro-2-(2-pyridyl)ethylazide

HRID 397472노트

반응식

HRID 397472 반응식
FC(F)(F)S(O[CH2:7][C:8]([F:16])([F:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+].O>CN(C=O)C>[F:15][C:8]([F:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:7][N:19]=[N+:20]=[N-:21]

참가 물질

5

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 110662242,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate

생성물 1

HCID 118054052,2-Difluoro-2-(2-pyridyl)ethylazide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a stirred solution of 5.5 g of 2,2-difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate I-1-4 in 70 mL of DMF was added 6.74 g (104 mmol) of sodium azide under Ar. The mixture was heated to 60° C. overnight. A second batch was run in the same manner, and after cooling to rt, both reactions were poured into 600 mL of water, and extracted with 3×500 mL of ether. The combined extracts were washed with brine, dried over Na2SO4 and concentrated at reduced pressure to give an oil that was purified by SiO2 (10×6 cm) using hexane 1:3 EtOAc-hexane and 1:1 EtOAc-hexane. The product-containing fractions were concentrated at reduced pressure to give I-1-5 as a yellow oil: 1H NMR (CDCl3) δ4.05 (t, 2H), 7.4-7.45 (m, 1H), 7.73 (d, 1H), 7.83-7.89 (m, 1H), 8.67 (d, 1H).

후처리

  1. temperatureafter cooling to rt
  2. extractionextracted with 3×500 mL of ether
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated at reduced pressure
  6. customto give an oil that
  7. customwas purified by SiO2 (10×6 cm)
  8. concentrationThe product-containing fractions were concentrated at reduced pressure
  9. customto give I-1-5 as a yellow oil

출처 및 근거

ORD 기록
ord-801f46c07e284be2bee02ea1422fc40f
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610701B2

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