Potassium Phosphate, Tribasic → HCID 66576728, compound

HRID 572398Notes

Reaction equation

HRID 572398 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:3][CH2:2]1.Br[C:17]1[CH:27]=[CH:26][C:20]2[S:21][C:22]([F:25])=[C:23]([CH3:24])[C:19]=2[CH:18]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][N:12]([C:17]3[CH:27]=[CH:26][C:20]4[S:21][C:22]([F:25])=[C:23]([CH3:24])[C:19]=4[CH:18]=3)[C:11]2=[O:15])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-oneHCID 70982008HCID 70982008, compound

Product 1

HCID 66576728HCID 66576728, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropyl-pyridin-3-yl)-imidazolidin-2-one (I-1d: 100 mg, 0.4926 mmol) was reacted with 5-bromo-2-fluoro-3-methyl-benzo[b]thiophene (I-24c: 120 mg, 0.4926 mmol), copper iodide (9.3 mg, 0.04926 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (7.0 mg, 0.04926 mmol), potassium phosphate (313 mg, 1.4778 mmol) and 1,4-dioxane (5 ml) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in chloroform) afforded 120 mg of product (66% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (2% methanol in chloroform)

Sources & evidence

ORD record
ord-fbb9a2e635d346ddb10597ba4fb12a99
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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