Boron tribromide → HCID 68678485, compound

HRID 2233028Notes

Reaction equation

HRID 2233028 reaction equation
C([N:5]1[C:34](=[O:35])[N:8]2[CH:9]=[C:10]([C:17]3[CH:18]=[C:19]([CH:31]=[CH:32][CH:33]=3)[C:20]([NH:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:21])[N:11]=[C:12]([NH:13][CH:14]([CH3:16])[CH3:15])[C:7]2=[N:6]1)(C)(C)C.B(Br)(Br)Br>ClC(Cl)C>[CH:14]([NH:13][C:12]1[C:7]2[N:8]([C:34](=[O:35])[NH:5][N:6]=2)[CH:9]=[C:10]([C:17]2[CH:18]=[C:19]([CH:31]=[CH:32][CH:33]=2)[C:20]([NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])[N:11]=1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68677389HCID 68677389, compound

Product 1

HCID 68678485HCID 68678485, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 32 mg of the product of Step B and 251 mg of boron tribromide in dichloroethane (2.0 mL) was heated in a sealed tube at 125° C. After two h, the reaction was cooled to ambient temperature and the excess reagent carefully quenched by the addition of water. The resulting mixture was extracted with EtOAc and the organic layer washed with sat. sodium chloride, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to afford the title compound as a tan solid. MS (M+H+)=417.4.

Workup

  1. customthe excess reagent carefully quenched by the addition of water
  2. extractionThe resulting mixture was extracted with EtOAc
  3. washthe organic layer washed with sat. sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d08f2d2839e0425da660721df3d25f76
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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