Potassium Phosphate, Tribasic → 1-(4-Cyclopropyl-pyridin-3-yl)-3-(5-fluoro-benzo[b]thiophen-6-yl)-imidazolidin-2-one

HRID 523569Notes

Reaction equation

HRID 523569 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:18]([F:26])=[CH:19][C:20]2[CH:24]=[CH:23][S:22][C:21]=2[CH:25]=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:18]([F:26])=[CH:19][C:20]4[CH:24]=[CH:23][S:22][C:21]=4[CH:25]=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 70982589Benzo[b]thiophene, 6-bromo-5-fluoro-

Product 1

HCID 665767311-(4-Cyclopropyl-pyridin-3-yl)-3-(5-fluoro-benzo[b]thiophen-6-yl)-imidazolidin-2-oneYield 46.1%

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: 100 mg, 0.491 mmol) was reacted with 6-bromo-5-fluoro-benzo[b]thiophene (I-27d: 136 mg, 0.5901 mmol), copper iodide (28 mg, 0.147 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (21 mg, 0.147 mmol), potassium phosphate (313.9 mg, 1.7 mmol) and 1,4-dioxane (5 mL) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 80 mg of the product (46% yield).

Workup

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

Sources & evidence

ORD record
ord-ada7f6f1fa24431ab2c316defdb346ae
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

Loading…