Cesium carbonate → HCID 57516645, compound

HRID 1898622Notes

Reaction equation

HRID 1898622 reaction equation
[I:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:14][CH:15]1[CH2:17][CH2:16]1>CN(C=O)C>[CH:15]1([CH2:14][N:5]2[CH:6]=[C:2]([I:1])[N:3]=[CH:4]2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 178506559HCID 178506559, compound

Product 1

HCID 57516645HCID 57516645, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodo-1H-imidazole (800 mg, 4.12 mmol) in DMF (50 mL) was added cesium carbonate (5.37 g, 16.5 mmol) and (bromomethyl)cyclopropane (1.6 mL, 16.5 mmol). The reaction mixture was stirred at room temperature for 3 h then concentrated under reduced pressure. The residue was dissolved in EtOAc and washed sequentially with water, sat'd LiCl and sat'd NaCl. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (50% to 100% EtOAc/heptane) to isolate first 590 mg (58%) of 1-cyclopropylmethyl-4-iodo-1H-imidazole as a pale yellow oil followed by 227 mg (22%) of 1-cyclopropylmethyl-5-iodo-1H-imidazole as a pale yellow oil.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed sequentially with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (50% to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-befd6869d6534e00ad5be5407a4ddb2c
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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