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

HRID 2101446

반응식

HRID 2101446 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-96aee66d7e5344fe8ea4ebf1bfc4f029
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572910B2

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