Sodium Iodide → 1-(4-Fluorobenzoyl)-2-oxo-3-pyrrolidinecarbonitrile
Reaction equation
[C:1]([C:3]1[CH2:7][CH2:6][O:5][C:4]=1[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)#[N:2].[I-].[Na+]>CN(C)C=O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([N:8]2[CH2:6][CH2:7][CH:3]([C:1]#[N:2])[C:4]2=[O:5])=[O:17])=[CH:11][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a solution of N-(3-cyano-4,5-dihydrofuran-2-yl)-4-fluorobenzamide (5.0 g) obtained in Step E in N,N-dimethylformamide (30 mL) was added sodium iodide (6.5 g), and the mixture was stirred at 150° C. for 30 min. The solvent was evaporated under reduced pressure, and to the residue was added ice water. The resulting solid was collected by filtration, and washed with water. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), and the resulting solid was washed with diisopropyl ether to give the title compound (1.3 g).
Workup
- customThe solvent was evaporated under reduced pressure
- additionto the residue was added ice water
- filtrationThe resulting solid was collected by filtration
- washwashed with water
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
- washthe resulting solid was washed with diisopropyl ether
Sources & evidence
- ORD record
- ord-53acff91ea2745cf9fbd875b5355a078
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187453B2
Reaction notes
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