Potassium Carbonate → HCID 67818597, compound

HRID 1054539Notes

Reaction equation

HRID 1054539 reaction equation
[Cl:1][C:2]1[C:3]([C:16]([F:19])([F:18])[F:17])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[NH:7][C:6]=2[CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][Si:27]([CH2:30][CH2:31][O:32][CH2:33]Cl)([CH3:29])[CH3:28]>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:16]([F:17])([F:19])[F:18])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[N:7]([CH2:33][O:32][CH2:31][CH2:30][Si:27]([CH3:29])([CH3:28])[CH3:26])[C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178520563HCID 178520563, compound

Product 1

HCID 67818597HCID 67818597, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[6-chloro-5-(trifluoromethyl)-1H-1,3-benzodiazol-2-yl]butan-1-ol (5.88 g, 20.09 mmol) was dissolved in DMF (50 ml) and anhydrous potassium carbonate (3.47 g, 25.11 mmol) was added at r.t. under N2 and the reaction stirred for 1 hr. SEM-Cl (3.92 ml, 22.10 mmol) was added and the reaction stirred for 3 hrs. The reaction mixture was concentrated in vacuo, EtOAc (150 ml) was added and the mixture was washed with 50% sat. brine solution (3×200 ml). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography eluting with MeOH:DCM (1:99-6:94) to give the product as a light orange oil (4.95 g, 58%): MS (ESI+) for C18H26ClF3N2O2Si m/z 424.40 [M+H]+; LC purity 81% (ret. time, 2.41 min); 1H NMR (500 MHz, CHLOROFORM-d) δ ppm −0.11-0.01 (9H, m), 0.66-1.12 (2H, m), 1.60-1.87 (2H, m), 2.07 (2H, td, J=7.33, 2.05 Hz), 2.91-3.21 (2H, m), 3.43-3.61 (2H, m), 3.70 (2H, d, J=4.10 Hz), 5.49 (2H, d, J=17.81 Hz), 7.45-8.15 (2H, m)

Workup

  1. stirringthe reaction stirred for 3 hrs
  2. concentrationThe reaction mixture was concentrated in vacuo, EtOAc (150 ml)
  3. additionwas added
  4. washthe mixture was washed with 50% sat. brine solution (3×200 ml)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customThe product was purified by silica flash column chromatography
  10. washeluting with MeOH:DCM (1:99-6:94)

Sources & evidence

ORD record
ord-1eb27d8cde5c4dcaa17c42549e75a6bb
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

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