Bromine → HCID 91385505, compound

HRID 1800575Notes

Reaction equation

HRID 1800575 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][N:17]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[S-:24][C:25]#[N:26].[K+].BrBr>C(O)(=O)C>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[N:17]=[C:18]3[S:24][C:25]([NH2:26])=[N:22][C:19]3=[CH:20][CH:21]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 90991820HCID 90991820, compound

Product 1

HCID 91385505HCID 91385505, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of tert-butyl{3-[(5-aminopyridin-2-yl)oxy]-4-fluorophenyl}carbamate (2.50 g, 7.8 mmol) and potassium thiocyanate (2.92 g, 30 mmol) in acetic acid (30 mL) was added dropwise bromine (1.93 g, 12 mmol) under ice-cooling, and the mixture was stirred at room temperature overnight. The yellow insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate solution (100 mL), and the mixture was extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the title compound (1.92 g, 65%) as a pale-yellow amorphous.

Workup

  1. temperaturecooling
  2. filtrationThe yellow insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the residue was added saturated aqueous sodium hydrogen carbonate solution (100 mL)
  5. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-b929371542aa48179c56db95f76b5bdb
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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