Pyridine → HCID 59018177, compound

HRID 31159Notes

Reaction equation

HRID 31159 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:25](O)=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2.N1C=CC=CC=1>ClCCl>[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:25]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 232736625-Methoxyquinolin-8-ol

Product 1

HCID 59018177HCID 59018177, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulphonic anhydride (12 ml, 77.0 mmol) was added slowly, over approximately 5 minutes, to a stirred solution of 5-methoxy-quinolin-8-ol (Syn. Comm. 1997, 27(20), 3573-3579) (1.5 g, 8.6 mmol) and pyridine (5.5 ml, 68.5 mmol) in dichloromethane (34 ml) at 0° C., under nitrogen. The resulting mixture was allowed to warm to room temperature and stirred for a further 16 hours. The mixture was then partitioned between dichloromethane (100 ml) and saturated aqueous ammonium chloride solution (100 ml). The organic extract was further washed with water (100 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide a crude yellow solid. Purification by flash chromatography on silica gel, eluting with 5% ethyl acetate, 95% pentane, provided the title compound as a pale yellow solid (2.62 g, 99%). 1H-NMR (400 MHz, CDCl3): δ=4.02 (s, 3 H) 6.79 (d, 1 H) 7.50 (m, 2 H) 8.58 (dd, 1 H) 9.03 (dd, 1 H); LRMS: APCl+: m/z 308 [MH+].

Workup

  1. customThe mixture was then partitioned between dichloromethane (100 ml) and saturated aqueous ammonium chloride solution (100 ml)
  2. extractionThe organic extract
  3. washwas further washed with water (100 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide a crude yellow solid
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 5% ethyl acetate, 95% pentane

Sources & evidence

ORD record
ord-f770070bd5484eb38e028e69e41fef46
Source dataset
uspto-grants-2008_09
Patent number
US07425569B2

Reaction notes

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