Potassium Phosphate, Tribasic → HCID 66807156, compound

HRID 1843834Notes

Reaction equation

HRID 1843834 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][C:5](=[O:10])[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:6]1[CH2:7][CH2:8][C:9]2[S:1][CH:2]=[CH:3][C:4]=2[C:5]1=[O:10]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 203468586.7-dihydrothieno[3.2.c]pyridin-4(5H)-one

Product 1

HCID 66807156HCID 66807156, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in example 1, 6,7-dihydro-5H-thieno[3,2-c]pyridin-4-one (I-7d: 100 mg, 0.6527 mmol) was reacted with 3-iodo-4-methyl-pyridine (171.5 mg, 0.7832 mmol), 1,4-dioxane (20 mL), copper iodide (9.7 mg, 0.0652 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (27.8 mg, 0.1958 mmol) and potassium phosphate (346.3 mg, 1.6318 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 90 mg of the product (56.2% yield).

Workup

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

Sources & evidence

ORD record
ord-2111c991f2bf4159906b77ef53c29465
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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