HCID 57656007, compound → HCID 66706909, compound

HRID 911581Notes

Reaction equation

HRID 911581 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:7][S:8][C:4]=2[CH:3]=1.[Cu](C#N)[C:18]#[N:19]>CN1CCCC1=O.Cl>[C:18]([C:2]1[CH:16]=[CH:15][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:7][S:8][C:4]=2[CH:3]=1)#[N:19]

Participants

5

Reactant 2

HCID 57656007HCID 57656007, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 66706909HCID 66706909, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Combine 6-bromo-3-phenylbenzothiophene (0.5 g, 1.73 mmol) and copper cyanide (0.56 g, 6.23 mmol) and reflux 3 h in 1-methyl-2-pyrrolidinone (1.73 mL). Add ferric chloride (2.11 g, 7.79 mmol) in concentrated HCl (1.73 mL) and stir 1.5 h. Cool the mixture and partition between diethyl ether and brine. Dry the organic layer over Na2SO4, filter and evaporate onto silica gel. Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 3:2 gradient) to give the desired intermediate that is used without further-purification (0.27 g, 67%). MS (GCMS) m/z: 235 M+.

Workup

  1. temperatureCool the mixture
  2. custompartition between diethyl ether and brine
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate onto silica gel
  6. customPurify the residue by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 3:2 gradient)

Sources & evidence

ORD record
ord-329a2e0548874fa38b30541aec344e2f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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