Potassium Phosphate, Tribasic → HCID 68094624, compound

HRID 1843830Notes

Reaction equation

HRID 1843830 reaction equation
[S:1]1[C:5]2[C:6](=[O:10])[NH:7][CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1.I[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[CH3:18].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:18][C:17]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[N:7]1[CH2:8][CH2:9][C:4]2[CH:3]=[CH:2][S:1][C:5]=2[C:6]1=[O:10]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 218153465,6-Dihydrothieno[2,3-c]pyridin-7(4H)-one

Product 1

HCID 68094624HCID 68094624, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in example 1, 5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (I-5d: 130 mg, 0.849 mmol) was reacted with 3-iodo-4-methyl-pyridine (185 mg, 0.849 mmol), 1,4-dioxane (5 mL), copper iodide (16 mg, 0.0849 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (0.04 mL, 0.254 mmol) and potassium phosphate (538 mg, 2.54 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 105 mg of the product (51.4% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

Sources & evidence

ORD record
ord-81b9ee44602f45b8afdc4c381168718a
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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