Trifluoromethanesulfonic acid → 6-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine

HRID 369034

反応式

HRID 369034 の反応式
N[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[F:14][C:15]([F:21])([F:20])[S:16]([OH:19])(=[O:18])=[O:17].N([O-])=O.[Na+]>O>[F:14][C:15]([F:21])([F:20])[S:16]([O:19][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)(=[O:18])=[O:17]

参加物

5

反応物 3

HCID 62406Trifluoromethanesulfonic acidHCID 46725998-Methoxy-1,7-naphthyridin-6-amineHCID 23668193Sodium Nitrite

生成物 1

HCID 232846356-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a solution of 6-amino-8-methoxy-1,7-naphthyridine (19 g, 0.108 mol) in a 1:1 mixture of water and trifluoromethane sulfonic acid (380 ml) is carefully added a solution of sodium nitrite (11.2 g, 0.162 mol) in water (40 ml) at 0° C. After 1 h the cooling bath is removed and the reaction mixture stirred for an other hour at ambient temperature. Then, ethyl acetate (500 ml) is added and the solution is neutralized by adding sodium bicarbonate (4N, 1 l). The water phase is extracted again with ethyl acetate (3×500 ml). The organic solvent is evaporated and the crude product is purified by flash column chromatography on silica gel (20:3 toluene/acetone) affording the title compound. M+308; Melting point 99-101° C.

後処理

  1. customAfter 1 h the cooling bath is removed
  2. additionThen, ethyl acetate (500 ml) is added
  3. additionby adding sodium bicarbonate (4N, 1 l)
  4. extractionThe water phase is extracted again with ethyl acetate (3×500 ml)
  5. customThe organic solvent is evaporated
  6. customthe crude product is purified by flash column chromatography on silica gel (20:3 toluene/acetone)

出典と根拠

ORDレコード
ord-0752721364024996b548b4ef802fbc9c
出典データセット
uspto-grants-2000_10
特許番号
US06136821

関連ノート

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