Water → HCID 58790226, compound

HRID 2193722Notes

Reaction equation

HRID 2193722 reaction equation
I[C:2]1[N:3]([CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:4](I)=[C:5]([I:7])[N:6]=1.[Li]C(C)(C)C.O>C1COCC1>[I:7][C:5]1[N:6]=[CH:2][N:3]([CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 58790081HCID 58790081, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 58790226HCID 58790226, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4,5-triiodo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazole (166) (1.75 g, 3.22 mmol) in THF (32 mL) at −78° C. was added tBuLi (7.57 mL, 12.88 mmol) dropwise over a period of an hour. The reaction mixture was poured into water, extracted with EtOAc, and the organic extract was separated, dried over Na2SO4, and concentrated in vacuo to give the title compound 167 (0.9 g, 96% yield) as a dark yellow syrup. 1H NMR (DMSO-d6) δ (ppm): 7.59 (s, 1H), 7.36 (s, 1H), 4.02 (m, 2H), 2.78 (m, 2H), 2.42 (m, 4H), 1.63 (m, 4H). MS (m/z): 292.1 (M+H).

Workup

  1. extractionextracted with EtOAc
  2. extractionthe organic extract
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-464ff0cc369a4ae182ebc16b31cb6a03
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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