Trimethyltin chloride → HCID 67050696, compound

HRID 886309Notes

Reaction equation

HRID 886309 reaction equation
I[C:2]1[N:3]=[C:4]([CH3:16])[N:5]([CH2:7][CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH:6]=1.IC1N(CCOC2CCCCO2)C(C)=NC=1.C([Mg]Br)C.[CH3:37][Sn:38](Cl)([CH3:40])[CH3:39].[NH4+].[Cl-]>C(Cl)Cl>[CH3:16][C:4]1[N:5]([CH2:7][CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH:6]=[C:2]([Sn:38]([CH3:40])([CH3:39])[CH3:37])[N:3]=1

Participants

7

Reactant 5

HCID 14016Trimethyltin chlorideHCID 25517Ammonium ChlorideHCID 58204433HCID 58204433, compoundHCID 58204823HCID 58204823, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 67050696HCID 67050696, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a mixture of 4-iodo-2-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazole and 5-iodo-2-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazole (500 mg, 1.9 mmol) in DCM (10 mL) was added ethyl magnesium bromide (0.7 ml, 3 mol/L, 2.2 mmol) at −78° C. The mixture was allowed to warm up to about 10° C. slowly. After cooled to −78° C. again, trimethyltin chloride (2.2 mL, 1 mol/L, 2.2 mmol) was added dropwise. After addition, the mixture was allowed to slowly warm up to room temperature. The reaction mixture was poured into a saturate NH4Cl solution, and extracted with DCM. The combined organic layer was washed with water twice, dried over anhydrous Na2SO4 and concentrated to give 2-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(trimethylstannyl)-1H-imidazole (0.44 g, 63%) 1H NMR (CDCl3, 400 MHz): δ 6.93 (s, 1H), 4.54-4.53 (m, 1H), 4.05-4.03 (m, 2H), 3.97-3.93 (m, 1H), 3.61-3.59 (m, 2H), 3.45-3.39 (m, 1H), 2.44 (s, 3H), 1.66-1.47 (m, 6H), 0.26 (s, 9H). LC-MS, m/z 375 [M+H+], which was contaminated with some 2-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-5-(trimethylstannyl)-1H-imidazole.

Workup

  1. temperatureAfter cooled to −78° C. again
  2. additionAfter addition
  3. temperatureto slowly warm up to room temperature
  4. extractionextracted with DCM
  5. washThe combined organic layer was washed with water twice
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-011a4402cc8647fe9d1aa018c8ee3d70
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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