Tetrahydrofuran → HCID 11175146, compound

HRID 601651Notes

Reaction equation

HRID 601651 reaction equation
[H-].[Na+].O1CCCC1.[F:8][C:9]1[C:14]([N:15]2[C:19]([CH3:20])=[C:18]([C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[C:26](=[O:30])[C:25]([CH3:35])([O:31]C(C)=O)[CH2:24]4)[N:17]=[N:16]2)=[CH:13][CH:12]=[CH:11][N:10]=1>C(OCC)(=O)C>[F:8][C:9]1[C:14]([N:15]2[C:19]([CH3:20])=[C:18]([C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[C:26](=[O:30])[C:25]([OH:31])([CH3:35])[CH2:24]4)[N:17]=[N:16]2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11349506HCID 11349506, compound

Product 1

HCID 11175146HCID 11175146, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

At room temperature, 100 μl of 2M sodium hydride aqueous solution was added to 1 ml solution of tetrahydrofuran with 30 mg of 1-(2-fluoropyridine-3-yl)-4-(2-methyl-2-methylcarbonyloxy-1-oxoindane-5-yl)-5-methyl-1H-[1,2,3]triazole obtained in Example 51. The mixture was stirred at room temperature for 1 hour, diluted with ethyl acetate, washed with water and saturated saline solution, and dried with anhydrous sodium sulfate. The residues obtained by distilling out the solvents under reduced pressure were purified by silicagel column chromatography (hexane:ethyl acetate=80:20) to obtain 10 mg of the above compound as a white solid.

Workup

  1. washwashed with water and saturated saline solution
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe residues obtained
  4. distillationby distilling out the solvents under reduced pressure
  5. customwere purified by silicagel column chromatography (hexane:ethyl acetate=80:20)

Sources & evidence

ORD record
ord-25e155f02c1f4e65bb20f98115ca838b
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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