Potassium Phosphate, Tribasic → HCID 56940972, compound

HRID 1843891Notes

Reaction equation

HRID 1843891 reaction equation
[CH2:1]([N:3]1[C:7]2[C:8](=[O:12])[NH:9][CH2:10][CH2:11][C:6]=2[CH:5]=[CH:4]1)[CH3:2].I[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH3:20].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH2:1]([N:3]1[C:7]2[C:8](=[O:12])[N:9]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[CH3:20])[CH2:10][CH2:11][C:6]=2[CH:5]=[CH:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 66803487HCID 66803487, compound2×

Product 1

HCID 56940972HCID 56940972, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using similar reaction conditions as described in Example 5, 1-ethyl-1H-3-pyrrole-3-carbaldehyde was converted to 1-ethyl-1,4,5,6-tetrahydro-pyrrolo[2,3-c]pyridin-7-one. By employing analogous reaction conditions as described in Example 1, 1-ethyl-1,4,5,6-tetrahydro-pyrrolo[2,3-c]pyridin-7-one (75 mg, 0.4571 mmol) was reacted with 3-iodo-4-methyl-pyridine (100 mg, 0.457 mmol), 1,4-dioxane (5 mL), copper iodide (8.5 mg, 0.0457 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (0.021 mL, 0.137 mmol) and potassium phosphate (290 mg, 1.371 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 55 mg of the product (47.4% yield).

Workup

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

Sources & evidence

ORD record
ord-648a2d4f49254058afa98adf71757767
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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