Boron tribromide → HCID 69022979, compound

HRID 1865071Notes

Reaction equation

HRID 1865071 reaction equation
B(Br)(Br)Br.[CH2:5]([O:7][C:8]([C:10]1[N:11]([CH3:31])[CH:12]=[C:13]([C:29]#[N:30])[C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27]C)=[CH:17][CH:16]=1)=[O:9])[CH3:6]>C(Cl)Cl>[CH2:5]([O:7][C:8]([C:10]1[N:11]([CH3:31])[CH:12]=[C:13]([C:29]#[N:30])[C:14]=1[C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])=[CH:19][CH:20]=1)=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69022704HCID 69022704, compound

Product 1

HCID 69022979HCID 69022979, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add boron tribromide (1.60 g, 6.39 mmol) to 4-cyano-3-(2′-methoxy-biphenyl-4-yl)-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (2.10 g, 5.81 mmol, prepared in example E-17) in methylene chloride at 0° C. with stirring. The reaction is gradually allowed to warm to ambient temperature. After 18 hours, pour the reaction mixture into ice-water and extract with methylene chloride. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with acetonitrile:methylene chloride to provide the title compound. Mass spectrum (m/e): 345.1 (M−1).

Workup

  1. extractionextract with methylene chloride
  2. washwash with water and brine
  3. dry with materialdry over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash chromatography
  7. washeluting with acetonitrile

Sources & evidence

ORD record
ord-f2d5051d4d7c4b358b35e364f7d8b981
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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