Boron tribromide → HCID 135554909, compound

HRID 1489650Notes

Reaction equation

HRID 1489650 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:12][CH2:13][O:14][C:15]2[N:16]([CH3:28])[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=3)[CH:19]=2)[CH3:11])=[CH:4][CH:3]=1.B(Br)(Br)Br.C(O)(=O)[C@@H]([C@H](C(O)=O)O)O>ClCCl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:12][CH2:13][O:14][C:15]2[N:16]([CH3:28])[N:17]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)[CH:19]=2)[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25134Boron tribromideHCID 444305L-Tartaric acidHCID 54044030HCID 54044030, compound

Product 1

HCID 135554909HCID 135554909, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.8 g of 3-(2-[N-(2-(4-chlorophenyl)-ethyl)-N-methylamino]-ethyloxy}-5-(-4-methoxyphenyl)-2-methylpyrazole (see Example 24) were dissolved in 100 ml of dichloromethane. 10 ml of a 1 molar solution of boron tribromide in dichloromethane were added to the solution. The reaction mixture was allowed to stand for 12 hours and then placed in water and extracted with dichloromethane. The aqueous phase was separated, rendered alkaline and extracted three times with a mixture of dichloromethane and methanol, and the combined organic phases were dried and concentrated. The crude title compound obtained as an oil was purified by chromatography on silica gel using dichloromethane/methanol. The purified title compound was reacted in accordance with the method described in Example 4C) with an equimolar quantity of L-(+)-tartaric acid to form a salt, and the resulting salt was crystallized from a mixture of diethyl ether and isopropanol. 1.15 g of 3-{2-[N-(2-(4-chlorophenyl)-ethyl)-N-methylamino]-ethyloxy}-5-(4-hydroxyphenyl)-2-methylpyrazole x 1.3 hydrogen tartrate were obtained having a melting point of 90° to 91° C.

Workup

  1. extractionextracted with dichloromethane
  2. customThe aqueous phase was separated
  3. extractionextracted three times
  4. additionwith a mixture of dichloromethane and methanol
  5. customthe combined organic phases were dried
  6. concentrationconcentrated
  7. customThe crude title compound obtained as an oil
  8. customwas purified by chromatography on silica gel
  9. customThe purified title compound
  10. customwas reacted in accordance with the method
  11. customto form a salt
  12. customthe resulting salt was crystallized from a mixture of diethyl ether and isopropanol

Sources & evidence

ORD record
ord-e92dc065084f4139b096ac37a1f5bf68
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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