Bromine → HCID 86657978, compound

HRID 2366808Notes

Reaction equation

HRID 2366808 reaction equation
[S-:1][C:2]#[N:3].[K+].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]2[CH:14]=[C:15]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:16]=[CH:17][C:18]=2[CH3:19])=[N:10][CH:11]=1.BrBr>C(O)(=O)C>[NH2:3][C:2]1[S:1][C:11]2[C:6]([N:5]=1)=[CH:7][CH:8]=[C:9]([O:12][C:13]1[CH:14]=[C:15]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:16]=[CH:17][C:18]=1[CH3:19])[N:10]=2

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 86657977HCID 86657977, compound

Product 1

HCID 86657978HCID 86657978, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of potassium thiocyanate (62.9 g, 647 mmol) in acetic acid (500 ml) was added benzyl {3-[(5-aminopyridin-2-yl)oxy]-4-methylphenyl}carbamate (56.5 g, 162 mmol), and a solution of bromine (27.1 g, 170 mmol) in acetic acid (100 mL) was added dropwise. The reaction mixture was stirred at room temperature for 18 hr, and the insoluble material was filtered off through a celite pad. The filtrate was concentrated under reduced pressure, and the obtained residue was diluted with ethyl acetate (500 mL) and washed with saturated aqueous sodium hydrogen carbonate solution (300 mL). The obtained aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with saturated brine (100 mL), and purified by silica gel (ethyl acetate). The obtained solution was concentrated under reduced pressure, and the crystals precipitated during concentration were collected by filtration to give the title compound (48.4 g, 74%) as a pale-brown solid.

Workup

  1. filtrationthe insoluble material was filtered off through a celite pad
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionthe obtained residue was diluted with ethyl acetate (500 mL)
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution (300 mL)
  5. extractionThe obtained aqueous layer was extracted with ethyl acetate (100 mL)
  6. washThe combined organic layer was washed with saturated brine (100 mL)
  7. custompurified by silica gel (ethyl acetate)
  8. concentrationThe obtained solution was concentrated under reduced pressure
  9. customthe crystals precipitated during concentration
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-0c52d81fddb2446d9880845a4449ff6e
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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