Water → HCID 14989563, compound

HRID 1111106Notes

Reaction equation

HRID 1111106 reaction equation
FC(F)(F)S([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])(=O)=O.[Br:19][C:20]1[CH:21]=[CH:22][C:23](=O)[NH:24][CH:25]=1.N1C(C)=CC=CC=1C.O>ClCCl>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])=[N:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 5995285-Bromo-2-hydroxypyridineHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

Product 1

HCID 14989563HCID 14989563, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triisopropylsilyl trifluoromethanesulfonate (65.4 g) was added dropwise to a solution of 5-bromo-2(1H)-pyridinone (33.8 g) and 2,6-lutidine (31.1 g) in 775 ml of dichloromethane at 0° C. The resulting solution was stirred for 15 minutes, and then it was poured into water and the layers were separated. The aqueous phase was extracted with dichloromethane, and the combined organic layers were dried over magnesium sulfate and concentrated to give a liquid. The product was slurried with silica gel and hexanes. Filtration gave 64.6 g of oil.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a liquid
  6. filtrationFiltration

Sources & evidence

ORD record
ord-3a947ffa35dd4f0fa4d4a06cc5c59667
Source dataset
uspto-grants-1990_12
Patent number
US04978663

Reaction notes

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