Boron tribromide → HCID 178492397, compound

HRID 2262759Notes

Reaction equation

HRID 2262759 reaction equation
C[O:2][C:3]1[C:8]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[O:11])=[CH:7][CH:6]=[C:5]([O:23][CH3:24])[N:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:8]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:22])[F:21])[CH:14]=2)=[O:11])=[CH:7][CH:6]=[C:5]([O:23][CH3:24])[N:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 2741388HCID 2741388, compound

Product 1

HCID 178492397HCID 178492397, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(2,6-dimethoxy-pyridin-3-yl)-3-(3-trifluoromethyl-phenyl)-urea (0.5 g) was suspended in dry dichloromethane (10 ml), BBr3 (0.14 ml) was added and the solution stirred at room temperature. After 5 hours more BBr3 (50 μl) was added and after a further hour the reaction was diluted with more dichloromethane and quenched with ice-water. The mixture was extracted with ethyl acetate, dried over MgSO4, filtered and concentrated to provide a light purple residue. This was preloaded onto silica and chromatographed to provide 1-(2-Hydroxy-6-methoxy-pyridin-3-yl)-3-(3-trifluoromethyl-phenyl)-urea as a white solid (210 mg). Mp.=223-224° C.

Workup

  1. customquenched with ice-water
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a light purple residue
  7. customchromatographed

Sources & evidence

ORD record
ord-76f501af54a94526852fb4dbfc9c191a
Source dataset
uspto-grants-2010_12
Patent number
US07851492B2

Reaction notes

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