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

HRID 1095753Notes

Reaction equation

HRID 1095753 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)quinoline

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 (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 (35 g)

Sources & evidence

ORD record
ord-d67411fbe7b5482291ef8d51b59cd714
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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