Potassium Carbonate → HCID 67383577, compound

HRID 335821Notes

Reaction equation

HRID 335821 reaction equation
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

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 109245324-Bromo-2-iodophenolHCID 67383095HCID 67383095, compound

Product 1

HCID 67383577HCID 67383577, compound

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f55f0b01df4b412dbd521f8ed8148d38
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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