Pyridine → HCID 59018177、化合物

HRID 970027ノート

反応式

HRID 970027 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 59018177HCID 59018177、化合物収率 99.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-6b5fa2043ffb4acb90b8a0df07c24df2
出典データセット
uspto-grants-2007_12
特許番号
US07309712B2

反応ノート

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