Trifluoroacetic acid → 2-Fluoro-5-(4-(methylthio)benzyl)pyridine

HRID 1811891

반응식

HRID 1811891 반응식
[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)=[CH:6][N:7]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59548286(6-Fluoropyridin-3-yl)(4-(methylthio)phenyl)methanol

생성물 1

HCID 595483662-Fluoro-5-(4-(methylthio)benzyl)pyridine수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of (6-fluoropyridin-3-yl)(4-(methylthio)phenyl)methanol (1.716 g, 6.88 mmol) in DCM (3.0 mL) was treated with trifluoroacetic acid (2.56 mL, 34.4 mmol) resulting in a green solution. The mixture was stirred for 5 min, and then triethylsilane (3.30 mL, 20.65 mmol) was added dropwise. The green color dissipated rapidly to give a straw colored solution, and a brief exotherm was observed (DCM started refluxing). The mixture was stirred for 30 min, and then extracted into DCM from saturated aqueous NaHCO3. The DCM extracts were dried (MgSO4) and purified by flash chromatography (5% to 7.5% EtOAc/hexane) to give 2-fluoro-5-(4-(methylthio)benzyl)pyridine (89% over 2 steps) as a colorless oil. 1H NMR (400 MHz, d6-DMSO) δ 8.15 (s, 1H); 7.81 (t, J=8.22 Hz, 1H); 7.20 (s, 4H); 7.10 (d, J=8.41 Hz, 1H); 3.94 (s, 2H); 2.44 (s, 3H). 19F NMR (376 MHz, d6-DMSO) 6-72.37 (s, 1 F). m/z (ESI, +ve ion) 234.0 (M+H)+.

후처리

  1. customresulting in a green solution
  2. customto give a straw colored solution
  3. stirringThe mixture was stirred for 30 min
  4. extractionextracted into DCM from saturated aqueous NaHCO3
  5. dry with materialThe DCM extracts were dried (MgSO4)
  6. custompurified by flash chromatography (5% to 7.5% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-c573ac0b82bf40e08066981f09e47a5c
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

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