Dichloromethane → N-[6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3-chloro-5-hydroxy-phenyl)-N-methyl-isobutyramide

HRID 1951665Notes

Reaction equation

HRID 1951665 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:23])[C:9](=[O:22])[C:10]([C:13]2[CH:18]=[C:17]([O:19]C)[CH:16]=[C:15]([Cl:21])[CH:14]=2)([CH3:12])[CH3:11])=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH:3]=1.C(Cl)Cl>O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:23])[C:9](=[O:22])[C:10]([C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([Cl:21])[CH:14]=2)([CH3:11])[CH3:12])=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH:3]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86597669N-[6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3-chloro-5-methoxy-phenyl)-N-methyl-isobutyramide

Product 1

HCID 86597668N-[6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3-chloro-5-hydroxy-phenyl)-N-methyl-isobutyramideYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.10 g (2.37 mmol) N-[6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3-chloro-5-methoxy-phenyl)-N-methyl-isobutyramide in 20 ml CH2Cl2 4.74 ml (4.74 mmol) BBr3 (1 M in CH2Cl2) was added at 0° C. The reaction mixture was allowed to reach ambient temperature and stirred for 6 h After addition of 50 ml water the mixture was extracted three times with 60 ml CH2Cl2. The combined organic solvents were dried (Na2SO4), filtered and evaporated. The residue was purified by flash-chromatography (SiO2, CH2Cl2/ethyl acetate 4:1) to give 0.70 g (65%) of the title compound as a white foam. MS m/e (%): 449.1 (M+H+, 100).

Workup

  1. customto reach ambient temperature
  2. extractionwas extracted three times with 60 ml CH2Cl2
  3. dry with materialThe combined organic solvents were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash-chromatography (SiO2, CH2Cl2/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-783653c367ec4513b97e04458271bcc6
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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