Pyridine → HCID 59018177, compound

HRID 970027Notes

Reaction equation

HRID 970027 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-6b5fa2043ffb4acb90b8a0df07c24df2
Source dataset
uspto-grants-2007_12
Patent number
US07309712B2

Reaction notes

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