Trifluoroacetic anhydride → 3-(4-Bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide

HRID 1409501노트

반응식

HRID 1409501 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][C:16]2[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:6]([CH:14]=1)[C:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[O:8].C(N)(N)=[O:24].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][C:16]2[C:17]([F:22])=[N+:18]([O-:24])[CH:19]=[CH:20][CH:21]=2)=[C:6]([C:7](=[O:8])[N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:14]=1

참가 물질

5

반응물 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 667282945-bromo-N,N-diethyl-2-(2-fluoropyridin-3-yloxy)benzamide

생성물 1

HCID 667281373-(4-Bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-bromo-N,N-diethyl-2-(2-fluoropyridin-3-yloxy)benzamide (1.4 g, 3.81 mmol) and urea peroxide (1.076 g, 11.44 mmol) in 10 mL of DCM at 0 C was added dropwise trifluoroacetic anhydride (1.601 mL, 11.44 mmol) and the resulting reaction was stirred overnight. LCMS showed only less than 50% of desired conversion. The mixture was evaporated to dryness, quenched with Sat. NaHCO3, extracted with EA, dried over Na2SO4, filtered and evaporated to dryness. CC (DCM to DCM/EA=3:1 to DCM/MeOH=100:2 to 100:5 to 100:10) gave 3-(4-bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide as an off white solid.

후처리

  1. customthe resulting reaction
  2. customThe mixture was evaporated to dryness
  3. customquenched with Sat. NaHCO3
  4. extractionextracted with EA
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-b70e3fb6b6ed474c8dca00d2a685e9be
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921363B2

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