Ethylenediamine → 4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-propenyl)-1H-imidazole

HRID 242381Notes

Reaction equation

HRID 242381 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[N:21]=[CH:22][NH:23][CH:24]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:26]([CH3:28])=[CH2:27].C(N)CN.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu](I)I>[Si:1]([O:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]([CH2:28][CH:26]=[CH2:27])[CH:24]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 112022-BromopropeneHCID 62657Potassium Phosphate, TribasicHCID 178455513HCID 178455513, compound

Product 1

HCID 892621944-(tert-Butyldiphenylsilyloxymethyl)-1-(2-propenyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

4-(tert-Butyldiphenylsilyloxymethyl)-1H-imidazole (1.000 g), 2-bromo-1-propene (1.04 mL), ethylenediamine (0.40 mL), copper iodide (0.28 g) and tripotassium phosphate (1.30 g) were suspended in dioxane (10 mL), and reacted in a microwave reactor (product name: Initiator, manufactured by Biotage, Ltd.) at 140° C. for 5 hours. The reaction solution was filtered using Celite to filter off the insolubles, followed by concentration of the mother liquor. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→100%) using silica gel column (product name: Hi-Flash column 3 L, manufactured by Yamazen Corporation) to afford the title compound (0.350 g).

Workup

  1. customreacted in a microwave reactor (product name: Initiator, manufactured by Biotage, Ltd.) at 140° C. for 5 hours
  2. filtrationThe reaction solution was filtered
  3. filtrationto filter off the insolubles
  4. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→100%)

Sources & evidence

ORD record
ord-1e9e9a1b67fd45548246db53417de091
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

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