Bromine → HCID 90861006, compound

HRID 1800587Notes

Reaction equation

HRID 1800587 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]=2)[C:11]([F:22])=[CH:10][C:9]=1[F:23])([CH3:4])([CH3:3])[CH3:2].[S-:25][C:26]#[N:27].[K+].BrBr>C(O)(=O)C>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:16]=[C:17]3[S:25][C:26]([NH2:27])=[N:21][C:18]3=[CH:19][CH:20]=2)[C:11]([F:22])=[CH:10][C:9]=1[F:23])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 90941707HCID 90941707, compound

Product 1

HCID 90861006HCID 90861006, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of tert-butyl{5[(5-aminopyridin-2-yl)oxy]-2,4-difluorophenyl}carbamate (8.70 g, 25.8 mmol) and potassium thiocyanate (9.72 g, 100 mmol) in acetic acid (100 mL) was added dropwise bromine (6.39 g, 40 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 (400 mL), and the mixture was extracted with ethyl acetate (300 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 (9.00 g, 88%) 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 (400 mL)
  5. extractionthe mixture was extracted with ethyl acetate (300 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-2b5b10bbff0747b3b645fab26a9882f2
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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