Isobutylamine → HCID 11152321, compound

HRID 1594381Notes

Reaction equation

HRID 1594381 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([N+:15]#[C-:16])=[C:6](Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Br:13])[CH3:2].C(N(CC)CC)C.[CH2:25]([NH2:29])[CH:26]([CH3:28])[CH3:27]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:5]1[N:15]=[CH:16][N:29]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Br:13])=[O:17])[CH3:2]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 8471TriethylamineHCID 86047800HCID 86047800, compound

Product 1

HCID 11152321HCID 11152321, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0.5 M solution of 3-bromo-3-(2-bromophenyl)-2-isocyano-acrylic acid ethyl ester (2.55 g; 7.11 mM) and triethylamine (990 μl; 7.11 mM) in dimethylformamide (DMF) is added drop by drop at room temperature with isobutylamine (850 μl; 8.53 mM). The reaction mixture is kept at room temperature until complete reaction, then is quenched with a NaHCO3 saturated solution, extracted with ethyl acetate, washed with water, dried over Na2SO4, and evaporated under reduced pressure. The crude is purified by flash chromatography, eluting with ethyl acetate, to obtain 1.77 g of 5-(2-bromophenyl)-1-isobutyl-1H-imidazole-4-carboxylic acid ethyl ester. (Yield: 71%).

Workup

  1. customThe reaction mixture is kept at room temperature until complete reaction
  2. customis quenched with a NaHCO3 saturated solution
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude is purified by flash chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c36d3c9cdfcf46ef8b0f9e82b2fd00cf
Source dataset
uspto-grants-2007_11
Patent number
US07301027B2

Reaction notes

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