Tributyltin Chloride → 5-Tributylstannyl-4-iodo-1-methyl-1H-imidazole

HRID 32605

Reaction equation

HRID 32605 reaction equation
[I:1][C:2]1[N:3]=[CH:4][N:5]([CH3:8])[C:6]=1I.C([Mg]Br)C.[CH2:13]([Sn:17](Cl)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].[NH4+].[Cl-]>C1COCC1.O>[CH2:22]([Sn:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[C:6]1[N:5]([CH3:8])[CH:4]=[N:3][C:2]=1[I:1])[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 3323874,5-Diiodo-1-methyl-1H-imidazoleHCID 178418443HCID 178418443, compound

Product 1

HCID 179657855-Tributylstannyl-4-iodo-1-methyl-1H-imidazoleYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4,5-Diiodo-1-methyl-1H-imidazole (40.0 g) was stirred in anhydrous THF (560 mL) at ambient temperature and ethylmagnesium bromide (3M in ether, 42.0 mL) was added over 20 minutes under an inert atmosphere. The resulting white precipitate was stirred for 30 minutes then tributyltin chloride (34.2 mL) added dropwise. The resulting clear solution was stirred for 1 hr, then saturated aqueous NH4Cl (50 mL) and water (300 mL) were added. The reaction mixture was extracted with DCM (500 mL), washed with water (3×300 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica eluting with hexane:EtOAc (1:1) to afford the title compound as a colourless oil (45.1 g, 76%);

Workup

  1. stirringThe resulting clear solution was stirred for 1 hr
  2. extractionThe reaction mixture was extracted with DCM (500 mL)
  3. washwashed with water (3×300 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica eluting with hexane:EtOAc (1:1)

Sources & evidence

ORD record
ord-863c4d54d6fd4c958f94e004628de8c3
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Linked notes

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