Dichloromethane → HCID 59170887, compound

HRID 1362604Notes

Reaction equation

HRID 1362604 reaction equation
C(Cl)Cl.[C:4]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][NH:11][C:12](=[O:29])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]3)=[C:17]([O:27]C)[CH:16]=2)[CH:5]=1.B(Br)(Br)Br>C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[C:4]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][NH:11][C:12](=[O:29])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]3)=[C:17]([OH:27])[CH:16]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 11718775HCID 11718775, compound

Product 1

HCID 59170887HCID 59170887, compoundYield 17.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a methylene chloride solution (3 mL) of (E)-N-biphenyl-3-ylmethyl-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)acrylic acid amide (100 mg) obtained in Example 121, boron tribromide (1M pentane solution, 1.18 mL) was added dropwise at −78° C. and the reaction solution was agitated at room temperature for 6 hours. The reaction solution was diluted with a saturated sodium bicarbonate solution and ethyl acetate, and the organic layer was partitioned. The organic layer was concentrated under reduced pressure after dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (elution solvent: chloroform-methanol system), and 16.5 mg of the title compound was obtained.

Workup

  1. customthe organic layer was partitioned
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. dry with materialafter dried over anhydrous magnesium sulfate
  4. customThe residue was purified by silica gel column chromatography (elution solvent: chloroform-methanol system)

Sources & evidence

ORD record
ord-179afaf28fcc411e9b443ac3f9fd14ee
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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