Cesium carbonate → HCID 67050696, compound

HRID 1498321Notes

Reaction equation

HRID 1498321 reaction equation
IC1N=C(C)NC=1.C([O-])([O-])=O.[Cs+].[Cs+].BrCCOC1CCCCO1.[I:24][C:25]1[N:26]=[C:27]([CH3:39])[N:28]([CH2:30][CH2:31][O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[CH:29]=1.C([Mg]Br)C.[CH3:44][Sn:45](Cl)([CH3:47])[CH3:46]>CN(C=O)C.C(Cl)Cl>[I:24][C:25]1[N:26]=[C:27]([CH3:39])[N:28]([CH2:30][CH2:31][O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[CH:29]=1.[CH3:39][C:27]1[N:28]([CH2:30][CH2:31][O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[CH:29]=[C:25]([Sn:45]([CH3:47])([CH3:46])[CH3:44])[N:26]=1

Participants

10

Reactant 6

HCID 10796Cesium carbonateHCID 14016Trimethyltin chlorideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 58204823HCID 58204823, compoundHCID 178418443HCID 178418443, compoundHCID 178433060HCID 178433060, compound

Product 2

HCID 58204823HCID 58204823, compoundHCID 67050696HCID 67050696, compoundYield 124.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

4-Iodo-2-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazole was prepared by reaction of 4-iodo-2-methyl-1H-imidazole, Cs2CO3, and 2-(2-Bromo-ethoxy)-tetrahydro-pyran in DMF. To a mixture of 4-Iodo-2-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazole (500 mg, 1.9 mmol) in DCM (10 mL) was added ethylmagnesium bromide (0.7 ml, 3 mol/L, 2.2 mmol) at −78° C. The temperature of the mixture was allowed to warm up to about 10° C. slowly and cooled again. Trimethyltin chloride (2.2 ml, 1 mol/1, 2.2 mmol) was added dropwise at −78° C. After the addition, the temperature was allowed to slowly warm up to room temperature. The reaction mixture was pouted into saturate NH4Cl solution, then extracted with DCM, The organic was washed with water twice, dried over anhydrous Na2SO4, concentrated to give 0.44 g of 2-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(trimethyl stannyl)-1H-imidazole. Yield=63%. 1H NMR (CDCl3, 400 MHz): δ 7.04 (s, 1 H, ArH), 3.71 (s, 2 H), 2.43 (s, 3 H), 1.24-1.20 (m, 6 H), 0.88 (s, 9 H), 0.29 (s, 6 H), 0.06 (s, 9 H). LC-MS: m/z=375 [M+H+]

Workup

  1. temperaturecooled again
  2. additionAfter the addition
  3. temperatureto slowly warm up to room temperature
  4. concentrationinto saturate NH4Cl solution
  5. extractionextracted with DCM
  6. washThe organic was washed with water twice
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-74fdbd9c5fb341f5af1f19d492c44a43
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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