Potassium Carbonate → 1-(4-Methyl-pyridin-3-yl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-imidazolidin-2-one

HRID 80051Notes

Reaction equation

HRID 80051 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[N:19]=[CH:18]2.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][N:10]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[N:19]=[CH:18]3)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 58259768HCID 58259768, compoundHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 687857481-(4-Methyl-pyridin-3-yl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-imidazolidin-2-oneYield 97,688.703%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 0.095 g, 0.00058 mol) was reacted with 5-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (0.170 g, 0.00058 mmol), 1,4-dioxane (10 mL), copper iodide (0.011 g, 0.000051 mol), trans-1,2-diamino cyclohexane (0.018 g, 0.00016 mol) and potassium carbonate (0.134 g, 0.00106 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform) afforded 0.24 g of 1-(4-Methyl-pyridin-3-yl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-imidazolidin-2-one (97.5% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% MeOH in chloroform)

Sources & evidence

ORD record
ord-33f8b0b03c3d492bbbb024e0df80c24b
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

Loading…