Imidazole → 6-Fluoro-2-methyl-8-(triisopropylsilyloxy)quinoline

HRID 876406Notes

Reaction equation

HRID 876406 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([OH:12])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.N1C=CN=C1.FC(F)(F)S(O[Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])(=O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 667815176-Fluoro-8-hydroxy-2-methylquinoline

Product 1

HCID 667814296-Fluoro-2-methyl-8-(triisopropylsilyloxy)quinolineYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-fluoro-2-methylquinolin-8-ol (19.0 g, 107 mmol) was dissolved in methylene chloride (300 mL) and treated with 1H-imidazole (10.9 g, 160 mmol) and triisopropylsilyl trifluoromethanesulfonate (33.1 mL, 123 mmol). The reaction was stirred at ambient temperature for 13 hours. The reaction mixture was quenched with saturated NH4Cl and separated. The organic layer was washed twice with saturated NH4Cl, dried over Na2SO4 and concentrated in vacuo to provide the desired product (35 g).

Workup

  1. customThe reaction mixture was quenched with saturated NH4Cl
  2. customseparated
  3. washThe organic layer was washed twice with saturated NH4Cl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0aea6dc2d37c4d21b250f2a9d9d89a7f
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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