Sodium Iodide → HCID 11716540, compound
Reaction equation
Br[CH2:2][C@H:3]1[CH2:7][CH2:6][C@H:5]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[O:4]1.[Na+].[I-].[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22].C([O-])(O)=O.[Na+]>CS(C)=O>[CH2:21]([N:23]([CH2:2][C@H:3]1[CH2:7][CH2:6][C@H:5]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[O:4]1)[CH2:24][CH3:25])[CH3:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a vial under Ar was added trans-2-(bromomethyl)-5-(2′-methoxy-5′-fluorophenethyl)tetrahydrofuran (50 mg, 0.16 mmol), NaI (30 mg), diethylamine (55 mg, 0.75 mmol), NaHCO3 (120 mg), and dry DMSO (4 mL). The mixture thus obtained was heated to 50° C. under Ar for 72 h. After it was cooled to room temperature, the reaction mixture was poured into a separatory funnel containing sodium bicarbonate aqueous solution (sat. NaHCO3:H2O=1:1, 30 mL). The organic function was extracted with ethyl acetate (3×30 mL) and the combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. The solvent then was removed in vacuo and crude product thus obtained was purified by flash column chromatography (15% EtOAc in hexane, Rf=0.09) to give the product (14 mg, 28%) as an oil.
Workup
- customThe mixture thus obtained
- temperatureAfter it was cooled to room temperature
- additionthe reaction mixture was poured into a separatory funnel
- extractionThe organic function was extracted with ethyl acetate (3×30 mL)
- washthe combined organic layers were washed with brine (30 mL)
- dry with materialdried over sodium sulfate
- customThe solvent then was removed in vacuo and crude product
- customthus obtained
- customwas purified by flash column chromatography (15% EtOAc in hexane, Rf=0.09)
Sources & evidence
- ORD record
- ord-9aa1c56ab83641ed9ddf7ec7a041f837
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168635B2
Reaction notes
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