Tetrahydrofuran → 6-Anthracen-9-ylmethylene-1-(4-fluoro-phenyl)4a-methyl-1,4,4a,6,7,8-hexahydro-benzo[f]indazol-5-one

HRID 551304

反応式

HRID 551304 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[C:14]4CCCC(C=O)[C:13]4([CH3:23])[CH2:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH:24]1[C:37]2[C:28](=[CH:29][C:30]3[C:35]([C:36]=2[CH:38]=O)=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]=[CH:26][CH:25]=1.[CH2:40]1[CH2:44][O:43][CH2:42][CH2:41]1>>[CH:34]1[C:35]2[C:30](=[CH:29][C:28]3[C:37]([C:36]=2[CH:38]=[C:40]2[C:44](=[O:43])[C:13]4([CH3:12])[CH2:23][C:11]5[CH:10]=[N:9][N:8]([C:5]6[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=6)[C:16]=5[CH:15]=[C:14]4[CH2:42][CH2:41]2)=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:31]=[CH:32][CH:33]=1

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 695049-AnthracenecarboxaldehydeHCID 226059711-(4-Fluoro-phenyl)4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde

生成物 1

HCID 865896206-Anthracen-9-ylmethylene-1-(4-fluoro-phenyl)4a-methyl-1,4,4a,6,7,8-hexahydro-benzo[f]indazol-5-one収率 78%

反応条件

温度
0 °C

実験手順

In a 100 mL round bottom flask, aldehyde (207) (100 mg, 0.337 mmol) and anthracene-9-carboxaldehyde (349 mg, 1.69 mmol) were dissolved in 10 mL THF and cooled to 0° C. Lithium hexamethyldisilylamide (LHMS) (370 μL, 0.370 mmol) was added dropwise, and the solution was stirred at room temperature for 16 hours. The reaction was quenched with 5 mL of saturated aqueous ammonium chloride. The aqueous layer was extracted with ether (3×10 mL), and the pooled organic extracts were washed with brine (10 mL), dried (MgSO4) and then concentrated. Flash chromatography of the residue (0-25% EtOAc/hexanes) gave (269) (127.9 mg, 78%). 1H NMR (CDCl3) δ 1.45 (s, 3H) 2.19 (m, 1H) 2.35 (m, 2H) 2.47 (m, 1H) 3.04 (d, J=16.11 Hz, 1H) 3.15 (d, J=16.11 Hz, 1H) 6.25 (s, 1H) 7.13 (t, J=8.55 Hz, 2H) 7.47 (m, 6H) 7.55 (s, 1H) 7.87 (m, 1H) 8.00 (m, 3H) 8.39 (s, 1H) 8.43 (s, 1H); 13C NMR (CDCl3) 23.5, 27.2, 29.7, 30.2, 49.4, 110.4, 114.0, 115.9, 116.1, 125.0, 125.1, 125.2, 125.3, 125.5, 126.1, 127.5, 128.8, 128.9, 128.9, 129.0, 129.7, 131.1, 131.1, 135.5, 135.7, 135.7, 136.4, 138.5, 139.1, 145.2, 160.2, 162.6, 202.8.

後処理

  1. customThe reaction was quenched with 5 mL of saturated aqueous ammonium chloride
  2. extractionThe aqueous layer was extracted with ether (3×10 mL)
  3. washthe pooled organic extracts were washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-2a68b8636ad94b1abc70f3e190d5fcab
出典データセット
uspto-grants-2011_05
特許番号
US07947726B2

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