Imidazole → HCID 86663635, compound

HRID 1777186Notes

Reaction equation

HRID 1777186 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[CH:8]([OH:12])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.N1C=CN=C1.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C=O)C.CCOC(C)=O>[Si:22]([O:12][CH:8]1[CH2:7][CH2:6][CH2:5][C:4]2[N:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:9]1=2)([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 44116687HCID 44116687, compound

Product 1

HCID 86663635HCID 86663635, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-5,6,7,8-tetrahydroquinolin-5-ol (500 mg, 2.72 mmol) in DMF (10 mL) was treated with imidazole (260 mg, 3.81 mmol). After complete dissolution TBDMS-Cl was added and the resulting mixture was stirred at RT for 16 h. The reaction mixture was diluted with EtOAc (40 mL) and was washed with brine (5×). The organic layer was collected, dried with Na2SO4, filtered, and the solvent was evaporated at reduced pressure yielding the titled compound as an oil. Amount 760 mg. Yield 94%.

Workup

  1. additionwas added
  2. washwas washed with brine (5×)
  3. customThe organic layer was collected
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-e5657b040e264c33871057117e67d65e
Source dataset
uspto-grants-2016_02
Patent number
US09266855B2

Reaction notes

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