Potassium Carbonate → Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate

HRID 335821노트

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HRID 335821 반응식
F[C:2]1[N:11]=[C:10]([F:12])[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([I:25])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.FC(F)(F)S([O-])(=O)=O.[Ag+]>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:2]2[N:11]=[C:10]([F:12])[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[C:20]([I:25])[CH:19]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 109245324-Bromo-2-iodophenolHCID 67383095Methyl 2,6-difluoro-5-(trimethylsilyl)nicotinate

생성물 1

HCID 67383577Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate

시약·촉매·용매 2

HCID 76223Silver(I) trifluoromethanesulfonate촉매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

Methyl 2,6-difluoro-5-(trimethylsilyl)nicotinate (1.19 g, 4.85 mmol), 4-bromo-2-iodophenol (1.450 g, 4.85 mmol), and silver trifluoromethanesulfonate (1.496 g, 5.82 mmol) were dissolved in dry THF (40 mL) and treated with potassium carbonate (1.006 g, 7.28 mmol). The mixture was heated to 60° C. for 10 hours before being cooled to rt and filtered through a pad of celite. Water (100 mL) and diethyl ether (100 mL) were added to the filtrate and the phases were separated. The organics were dried with magnesium sulfate, filtered and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to DCM gradient) gave the desired methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate.

후처리

  1. temperaturebefore being cooled to rt
  2. filtrationfiltered through a pad of celite
  3. additionWater (100 mL) and diethyl ether (100 mL) were added to the filtrate
  4. customthe phases were separated
  5. dry with materialThe organics were dried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure
  8. customPurification

출처 및 근거

ORD 기록
ord-f55f0b01df4b412dbd521f8ed8148d38
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883782B2

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