Water → HCID 10131825, compound

HRID 1369626Notes

Reaction equation

HRID 1369626 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[Br:7][C:8]1[S:16][C:15]2[CH:14]=[CH:13][N:12]=[C:11](Cl)[C:10]=2[CH:9]=1.O>CN(C=O)C>[Br:7][C:8]1[S:16][C:15]2[CH:14]=[CH:13][N:12]=[C:11]([S:16][C:15]3[CH:14]=[CH:3][C:2]([CH3:5])=[CH:1][CH:10]=3)[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 177503902-Bromo-4-chlorothieno(3,2-c)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 10131825HCID 10131825, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Para-thiocresol (500 mg, 4 mmol) in DMF (10 mL) was treated with potassium t-butoxide (451 mg, 4 mmol) at room temperature, after 15 minutes cooled to 0° C., treated with 2-bromo-4-chlorothieno[3,2-c]pyridine (prepared in 6 steps according to the method of F. Eloy and A. Deryckere (Bull. Soc. Chim. Belg. 1970, 79,301) (1.0 g, 4.0 mmol), stirred at 0° C. for 2 hours and at room temperature for 12 hours, poured into water and extracted with diethyl ether. The extract was washed with water, dried (Na2SO4), and concentrated under vacuum. The residue was purified by flash chromatography on silica gel with 1:20 ethyl acetate-hexane to provide the title compound.

Workup

  1. customprepared in 6 steps
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography on silica gel with 1:20 ethyl acetate-hexane

Sources & evidence

ORD record
ord-a1bdfa6d2b8e4e0eb9e947243856c1e6
Source dataset
uspto-grants-2003_06
Patent number
US06579882B2

Reaction notes

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