HCID 57656007, compound → HCID 66706909, compound

HRID 2041448Notes

Reaction equation

HRID 2041448 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 Mt

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-fa7a8c6ef38a4834b62c11498b1bb6d3
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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