HCID 23000235, compound → HCID 23000277, compound

HRID 398342Notes

Reaction equation

HRID 398342 reaction equation
Br[C:2]1[C:3]([CH3:11])=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[Cu][C:13]#[N:14]>CN(C=O)C>[C:13]([C:2]1[C:3]([CH3:11])=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2)#[N:14]

Participants

4

Reactant 2

HCID 23000235HCID 23000235, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 23000277HCID 23000277, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A stirred mixture of 5-bromo-4-methyl-7-azaindoline (270 mg, 1.27 mmol) and copper (I) cyanide (135 mg, 1.5 mmol) in DMF (0.3 mL) was heated to 180° C. for 4 h. The reaction mixture was cooled and partitioned between 5% potassium cyanide solution and ethyl acetate. The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash column chromatography (50% ethyl acetate/hexanes) to give the title compound:

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between 5% potassium cyanide solution and ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-189e7a3844384af09466965ece8357bd
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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