Boron tribromide → HCID 136330668, compound

HRID 1797099Notes

Reaction equation

HRID 1797099 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]-pyridin-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-f99c5844cc9545c4af944b7b3bf7c6ea
Source dataset
uspto-grants-2006_04
Patent number
US07034044B2

Reaction notes

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