3-Fluorosulfonyl-6-methoxypyridazine → 3-Methoxy-6-(5-fluoro-3-methyl-benzofuran-2-sulfonyl)-pyridazine

HRID 22737

反応式

HRID 22737 の反応式
C([Li])CCC.[F:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][CH:13]=[C:12]([CH3:15])[C:11]=2[CH:16]=1.F[S:18]([C:21]1[N:22]=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)(=[O:20])=[O:19]>C1COCC1>[CH3:28][O:27][C:24]1[N:23]=[N:22][C:21]([S:18]([C:13]2[O:14][C:10]3[CH:9]=[CH:8][C:7]([F:6])=[CH:16][C:11]=3[C:12]=2[CH3:15])(=[O:20])=[O:19])=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 110306363-Fluorosulfonyl-6-methoxypyridazineHCID 116798475-Fluoro-3-methylbenzofuranHCID 178418339Butyllithium

生成物 1

HCID 116239443-Methoxy-6-(5-fluoro-3-methyl-benzofuran-2-sulfonyl)-pyridazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

n-Butyl lithium (2.5 M in hexane, 11 mmol, 4.83 mL) was added dropwise over 15 minutes to a solution of 5-fluoro-3-methyl benzofuran (11 mmol, 1.65 mg) in THF (20 mL) cooled to −78° C. To this was added 3-fluorosulfonyl-6-methoxy-pyridazine (11 mmol, 2.11 g) and stirred for 30 minutes. The reaction mixture was allowed to come to room temperature overnight and was then quenched with EtOAc (40 mL) and H2O (10 mL). The organic portion was collected, dried, filtered and the filtrate was evaporated to dryness to obtain a crude product, which was purified by silica gel chromatography (eluent:hexanes:EtOAc::4:1) to obtain the desired product: 3-methoxy-6-(5-fluoro-3-methyl-benzofuran-2-sulfonyl)-pyridazine (22%, 781 mg).

後処理

  1. waitto come to room temperature overnight
  2. customwas then quenched with EtOAc (40 mL) and H2O (10 mL)
  3. customThe organic portion was collected
  4. customdried
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness
  7. customto obtain a crude product, which
  8. customwas purified by silica gel chromatography (eluent:hexanes:EtOAc::4:1)

出典と根拠

ORDレコード
ord-ce80d6d96c1740208705ed3182bf24c3
出典データセット
uspto-grants-2005_02
特許番号
US06849629B2

関連ノート

読み込み中…