Ammonia → HCID 23130374, compound

HRID 2080135Notes

Reaction equation

HRID 2080135 reaction equation
Br[C:2]1[S:3][C:4]([CH:7]=[C:8]([CH3:10])[CH3:9])=[CH:5][CH:6]=1.[Cu](C#N)[C:12]#[N:13].N>CN(C)C=O>[CH3:9][C:8]([CH3:10])=[CH:7][C:4]1[S:3][C:2]([C:12]#[N:13])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 23130548HCID 23130548, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 23130374HCID 23130374, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-5-(2-methylpropenyl)-thiophene described in Preparation Example 143 (60 mg, 0.27 mmol) was dissolved in N,N-dimethylformamide (1 mL), copper cyanide (62 mg, 0.69 mmol) was added at 160° C., and the solution was stirred for 2 hours. The reaction solution was cooled, then, concentrated aqueous ammonia (5 mL) was added, and the solution was extracted with diethyl ether (10 mL). The organic layer was washed, dried over anhydrous magnesium sulfate, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5), and the title compound (15 mg, 0.092 mmol, 34%) was obtained as a colorless oil.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionthe solution was extracted with diethyl ether (10 mL)
  3. washThe organic layer was washed
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-9f872a3354bd45bd9e51c02417743cc8
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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