HCID 68494779, compound → HCID 68494206, compound

HRID 2381781Notes

Reaction equation

HRID 2381781 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13](Br)=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cu](C#N)[C:19]#[N:20]>CN(C)C=O>[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([C:19]#[N:20])=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68494779HCID 68494779, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 68494206HCID 68494206, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-benzyl-5-bromo-3-methylthiophene-2-carboxamide (1.00 g, 3.22 mmol) and copper cyanide (0.72 g, 8.06 mmol) in anhydrous N,N-dimethylformamide (15 mL) was stirred under nitrogen atmosphere at 150° C. for 7 h. The mixture was allowed to cool to ambient temperature, and partitioned between ethyl acetate (150 mL) and 14% aqueous ammonium hydroxide (100 mL). The organic layer was washed with 14% aqueous ammonium hydroxide (75 mL), water (75 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (0-25% ethyl acetate in hexanes) to afford the title compound as a colorless solid (0.31 g, 37%): 1H NMR (300 MHz, CDCl3) δ 7.41-7.29 (m, 6H), 6.13 (br s, 1H), 4.61 (d, J=5.7 Hz, 2H), 2.50 (s, 3H); MS (ES+) m/z 257.2 (M+1), 279.2 (M+23).

Workup

  1. temperatureto cool to ambient temperature
  2. custompartitioned between ethyl acetate (150 mL) and 14% aqueous ammonium hydroxide (100 mL)
  3. washThe organic layer was washed with 14% aqueous ammonium hydroxide (75 mL), water (75 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (0-25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0570a34d121445edbe814187ff2f4df0
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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