Methane → HCID 59198421, compound

HRID 1896524Notes

Reaction equation

HRID 1896524 reaction equation
Br[C:2]1[C:3]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:4]=2[C:5](=[O:8])[NH:6][CH:7]=1.[C:16]([Cu])#[N:17].Cl.C>CN1C(=O)CCC1.C(C(C)=O)C>[O:8]=[C:5]1[C:4]2[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:3]=2[C:2]([C:16]#[N:17])=[CH:7][NH:6]1

Participants

7

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 59198432HCID 59198432, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 59198421HCID 59198421, compound

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A suspension of 4-bromo[1]benzothieno[3,2-c]pyridin-1(2H)-one and CuCN (1.5 equiv) in NMP (0.41 M) was heated to reflux for 1.5 h. The mixture was cooled to room temperature and added to a stirring 2 N HCl solution. The mixture was stirred at room temperature for 1 h, filtered, washed with H2O and dried to give a dark grey solid. The crude product was heated to reflux with activated charcoal in methyl ethyl ketone (MEK) for 0.5 h and filtered through a short pad of silica gel, eluted with more MEK to give after concentration the title compound as a light brown solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. filtrationfiltered
  4. washwashed with H2O
  5. customdried
  6. customto give a dark grey solid
  7. filtrationfiltered through a short pad of silica gel
  8. washeluted with more MEK
  9. customto give
  10. concentrationafter concentration the title compound as a light brown solid

Sources & evidence

ORD record
ord-7bdc191e42834bd79dc83b099318ca33
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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