Boron tribromide → HCID 136330668, compound

HRID 965869Notes

Reaction equation

HRID 965869 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[N:16]=[C:15]([NH2:17])[CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:17][C:15]1[N:16]=[C:11]([CH:10]=[CH:9][C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69592016HCID 69592016, compound

Product 1

HCID 136330668HCID 136330668, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 6-[2-(4-methoxy-phenyl)-vinyl]-pyridine-2-yl-amine (1.0 g, 3.8 mmol) (example 3) in CH2Cl2 (60 ml) was treated with boron tribromide (2.4 ml, 25 mmol) and stirred for 72 hr. The precipitate was filtered, dissolved in AcOEt and washed with aqueous NaHCO3 solution. The organic phase was dried (Na2SO4), concentrated and the residue was chromatographed (SiO2 with CH2Cl2/MeOH/NH4OH=140/10/1) and crystallized to provide 0.20 g (25%) of the light yellow title compound. Mp. 224-225° C. (iPr2O), MS: m/e=213 (M+H+).

Workup

  1. filtrationThe precipitate was filtered
  2. dissolutiondissolved in AcOEt
  3. washwashed with aqueous NaHCO3 solution
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customthe residue was chromatographed (SiO2 with CH2Cl2/MeOH/NH4OH=140/10/1)
  7. customcrystallized

Sources & evidence

ORD record
ord-341539e350fe4ba3a9c628fd39b1df69
Source dataset
uspto-grants-2005_10
Patent number
US06951875B2

Reaction notes

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