Cyanogen Bromide → HCID 68663600, compound

HRID 452767Notes

Reaction equation

HRID 452767 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[NH:21][C:12]3[N:13]=[CH:14][CH:15]=[C:16]([C:17]([NH:19][NH2:20])=[O:18])[C:11]=3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:22]#[C:23]Br>CN(C)C(=O)C.C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][C:9]2[NH:21][C:12]3=[N:13][CH:14]=[CH:15][C:16]([C:17]4[O:18][C:23]([NH2:22])=[N:20][N:19]=4)=[C:11]3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 68663654HCID 68663654, compound

Product 1

HCID 68663600HCID 68663600, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent2×

Procedure

To a solution of 2-(2-phenylethyl)-1H-pyrrolo[2,3-b]pyridine-4-carbohydrazide (104 mg, 0.371 mmol) in N,N-dimethylacetamide (1 mL) was added a solution of cyanogen bromide (47 mg, 0.445 mmol) in N,N-dimethylacetamide (0.5 mL) at room temperature, and the resulting mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate), and recrystallized from N,N-dimethylformamide/water to give the title compound (50 mg, yield 44%) as pale-yellow crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)
  5. customrecrystallized from N,N-dimethylformamide/water

Sources & evidence

ORD record
ord-ac105f2646c64132a52f101beb542402
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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