Diisopropylamine → 3-Methoxy-6-(3-hydroxy-benzofuran-2-sulfonyl)-pyridazine

HRID 22739

反応式

HRID 22739 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[O:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[CH2:14]1.F[S:24]([C:27]1[N:28]=[N:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)(=[O:26])=[O:25]>C1COCC1>[CH3:34][O:33][C:30]1[N:29]=[N:28][C:27]([S:24]([C:14]2[O:13][C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]=2[OH:22])(=[O:26])=[O:25])=[CH:32][CH:31]=1

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 23556CoumaranoneHCID 110306363-Fluorosulfonyl-6-methoxypyridazineHCID 178418339Butyllithium

生成物 1

HCID 120717653-Methoxy-6-(3-hydroxy-benzofuran-2-sulfonyl)-pyridazine収率 17%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

n-Butyl lithium (12 mmol, 4.7 mL) was added dropwise to a solution of diisopropyl amine (12 mmol, 1.7 mL) in THF (5 mL) at −78° C. After 10 minutes, a solution of 3-coumaranone (10 mmol, 1.92 g) in THF (10 mL) was added. The temperature was maintained at −78° C. and stirred for 10 minutes. To this was added a solution of 3-fluorosulfonyl-6-methoxy-pyridazine. The reaction mixture was brought to room temperature over one hour and quenched with ammonium chloride (1 g) and extracted with EtOAc (2×25 mL). The EtOAc extract was washed with H2O, the organic layer was collected, dried, filtered and the filtrate was evaporated to a residue. This residue was purified by silica gel chromatography (eluent:hexanes:EtOAc::9:1) to yield 3-methoxy-6-(3-hydroxy-benzofuran-2-sulfonyl)-pyridazine (17%, 622 mg).

後処理

  1. waitThe reaction mixture was brought to room temperature over one hour
  2. customquenched with ammonium chloride (1 g)
  3. extractionextracted with EtOAc (2×25 mL)
  4. extractionThe EtOAc extract
  5. washwas washed with H2O
  6. customthe organic layer was collected
  7. customdried
  8. filtrationfiltered
  9. customthe filtrate was evaporated to a residue
  10. customThis residue was purified by silica gel chromatography (eluent:hexanes:EtOAc::9:1)

出典と根拠

ORDレコード
ord-d33ee970cf0e419886cf788bf37573d3
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…