Hydrochloric Acid → HCID 66801983, compound

HRID 1843858Notes

Reaction equation

HRID 1843858 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[CH2:14][CH2:13][NH:12][C:11](=[O:17])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.I[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[CH3:25].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>[Cu](I)I.O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:16][C:15]3[CH2:14][CH2:13][N:12]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][C:24]=4[CH3:25])[C:11](=[O:17])[C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 66801724HCID 66801724, compound

Product 1

HCID 66801983HCID 66801983, compoundYield 14.56%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 2-(4-fluoro-phenyl)-6,7-dihydro-5H-thieno[3,2-c]pyridin-4-one (I-14e: 150 mg, 0.61 mmol) was reacted with 3-iodo-4-methyl-pyridine (133 mg, 0.61 mmol), 1,4-dioxane (10 mL), copper iodide (11.6 mg, 0.061 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (25.98 mg, 0.183 mmol) and potassium phosphate (323.3 mg, 1.525 mmol) to afford the crude product which was treated with 6N HCl and filtered. The residue was washed with ethylacetate, neutralized with NaHCO3 solution and extracted with ethylacetate. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 30 mg of the product (14.56% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product which
  3. filtrationfiltered
  4. washThe residue was washed with ethylacetate
  5. extractionextracted with ethylacetate
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-00b5253055594dfe92bbd6b7885f1c2a
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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