Sodium Iodide → HCID 23589659, compound

HRID 503148Notes

Reaction equation

HRID 503148 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].Cl[CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[N:15]=[C:14]2[C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[CH:40]=1.[I-].[Na+]>O1CCCC1.O>[F:45][C:41]1[CH:40]=[C:39]([C:14]2[C:13]3[C:17](=[CH:18][CH:19]=[C:11]([CH2:10][O:1][C@H:2]4[CH2:6][CH2:5][O:4][CH2:3]4)[CH:12]=3)[N:16]([C:20]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:15]=2)[CH:44]=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 22260844HCID 22260844, compound

Product 1

HCID 23589659HCID 23589659, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 40 mg of (S)-3-hydroxytetrahydrofuran in tetrahydrofuran was added 15 mg of 60% sodium hydride (oily) in an atmosphere of nitrogen gas, and the mixture was stirred at room temperature for 15 minute. To the reaction mixture were added 150 mg of 5-(chloromethyl)-3-(3-fluorophenyl)-1-trityl-1H-indazole produced in Production Example I-32 and 45 mg of sodium iodide, followed by stirring at room temperature for five days. After adding water to the reaction mixture, it was extracted with 20 ml of ethyl acetate. The organic layer was sequentially washed with half-saturated aqueous sodium chloride solution and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The resulting crude product was purified and separated by silica gel column chromatography (ethyl acetate:toluene=0:1 to 1:9), to give 84 mg of the title compound as a white amorphous powder.

Workup

  1. stirringby stirring at room temperature for five days
  2. extractionwas extracted with 20 ml of ethyl acetate
  3. washThe organic layer was sequentially washed with half-saturated aqueous sodium chloride solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe resulting crude product was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:toluene=0:1 to 1:9)

Sources & evidence

ORD record
ord-480353c0f0b3434f85ee4bd283a739cc
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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