Triethylamine → HCID 68193679, compound

HRID 1911918Notes

Reaction equation

HRID 1911918 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([OH:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:27]([Si:30](Cl)([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])([CH3:29])[CH3:28]>C(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([O:13][Si:30]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:27]([CH3:29])[CH3:28])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139400Triisopropylsilyl chlorideHCID 178515626HCID 178515626, compound

Product 1

HCID 68193679HCID 68193679, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-iodophenyl)-1-(pyridin-2-yl)-1H-pyrazol-5-ol (0.5 mmol, 1 equivalent) was dissolved in CH2Cl2 (5 mL) to which 3 equivalents of triethylamine were then added. Under stream of nitrogen, 2 equivalents of triisopropylsilyl chloride (TIPSCl) were added thereto at 0° C., followed by stirring at room temperature. After 10 minutes, the solution was concentrated by distillation under reduced pressure and hexane was added thereto, followed by washing with a saturated NaHCO3 aqueous solution. After extraction with hexane twice, the organic layer was dried over anhydrous MgSO4, filtered, concentrated and then dried under vacuum to afford the title compound.

Workup

  1. additionwere then added
  2. customat 0° C.
  3. concentrationthe solution was concentrated by distillation under reduced pressure and hexane
  4. additionwas added
  5. washby washing with a saturated NaHCO3 aqueous solution
  6. extractionAfter extraction with hexane twice
  7. dry with materialthe organic layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried under vacuum

Sources & evidence

ORD record
ord-48edd4d2b80944b6a9cc8a4913a196d4
Source dataset
uspto-grants-2013_12
Patent number
US08604210B2

Reaction notes

Loading…