HCID 59829749, compound → HCID 59715391, compound

HRID 2223327Notes

Reaction equation

HRID 2223327 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH2:11][CH2:12][C:13]1[C:21]2[O:20][CH:19]=[CH:18][C:17]=2[CH:16]=[C:15](Br)[CH:14]=1.[C:24]([Cu])#[N:25]>CN(C=O)C.CCOC(C)=O>[C:24]([C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][C:5]2[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:2])=[O:23])[C:21]2[O:20][CH:19]=[CH:18][C:17]=2[CH:16]=1)#[N:25]

Participants

5

Reactant 2

HCID 59829749HCID 59829749, compoundHCID 178418546HCID 178418546, compound2×

Product 1

HCID 59715391HCID 59715391, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[2-(5-bromo-benzofuran-7-yl)-ethyl]-3-fluoro-benzoic acid methyl ester (1.5 g, 1.0 equiv) in DMF (16 mL) was added CuCN (0.7 g, 2.0 equiv). The resulting reaction mixture was allowed to heat for 16 hr before additional CuCN (0.7 g, 2.0 equiv) was added. After heating for 6 hr, the reaction mixture was allowed to cool to room temperature, diluted with EtOAc and filtered through celite. The filtrate was washed with saturated aqueous NaHCO3 and water and then dried over MgSO4, filtered, and concentrated. Purification of the residue by column chromatography (SiO2, EtOAc/hexane) gave the desired nitrile (0.6 g, 50%).

Workup

  1. customThe resulting reaction mixture
  2. additionwas added
  3. temperatureAfter heating for 6 hr
  4. filtrationfiltered through celite
  5. washThe filtrate was washed with saturated aqueous NaHCO3 and water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue by column chromatography (SiO2, EtOAc/hexane)

Sources & evidence

ORD record
ord-977a7cdd027f43838dedf2565a864db2
Source dataset
uspto-grants-2008_05
Patent number
US07375125B2

Reaction notes

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