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

HRID 1723917

Reaction equation

HRID 1723917 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
0 °C

Procedure

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 (LHMDS) (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) (127.9mg, 78%).

Workup

  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

Sources & evidence

ORD record
ord-93c95a43b99742018147724a0838f2de
Source dataset
uspto-grants-2009_02
Patent number
US07485660B2

Linked notes

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