Potassium Phosphate, Tribasic → 1-(4-Cyclopropylpyridin-3-yl)-3-(6-fluorobenzo[b]thiophen-5-yl)imidazolidin-2-one

HRID 523574Notes

Reaction equation

HRID 523574 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[C:25]([F:26])=[CH:24][C:20]2[S:21][CH:22]=[CH:23][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[C:25]([F:26])=[CH:24][C:20]4[S:21][CH:22]=[CH:23][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 709824575-Bromo-6-fluorobenzo[b]thiophene

Product 1

HCID 665767321-(4-Cyclopropylpyridin-3-yl)-3-(6-fluorobenzo[b]thiophen-5-yl)imidazolidin-2-oneYield 6%

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-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 90 g, 0.443 mmol) was reacted with 5-bromo-6-fluorobenzo[b]thiophene (I-28d: 102 mg, 0.443 mmol), 1,4-dioxane (4 mL), copper iodide (9 mg, 0.044 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (19 mg, 0.132 mmol) and potassium phosphate (282 mg, 1.329 mmol) to afford the crude product. Purification by preparative HPLC afforded 9 mg of the product (6% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-7bb2ffc67400454c83e1e592abb07da8
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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