Sodium Iodide → HCID 67855028, compound
Reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:9]=[C:8]2[N:10]=[C:11]([CH2:13][CH3:14])[NH:12][C:7]2=[C:6]([CH3:15])[CH:5]=1.[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27](CCl)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[I-].[Na+].[CH3:34]N(C=O)C>>[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([N:10]2[C:8]3=[N:9][C:4]([CH3:3])=[C:5]([CH3:34])[C:6]([CH3:15])=[C:7]3[N:12]=[C:11]2[CH2:13][CH3:14])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
6
Procedure
To a suspension of 0.503 g (12.5 mmol) of a 60% oil dispersion of sodium hydride in 20 mL of DMF was added 2.0 g (11.4 mmol) of the product of Step C and the mixture was stirred at room temperature. After 25 minutes, 2.92 g (12.5 mmol) of 4-benzyloxybenzyl chloride and a catalytic amount of sodium iodide were added and the reaction was stirred for an additional 4 hours. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried (MgSO4), filtered and evaporated. The residual oil was purified on a silica gel flash chromatography column eluted with 30% ethyl acetate/hexane to afford 3.33 g (79% ) of the title compound.
Workup
- stirringthe reaction was stirred for an additional 4 hours
- customThe reaction mixture was then partitioned between ethyl acetate and water
- customThe organic layer was separated
- washwashed with water, brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
- customThe residual oil was purified on a silica gel flash chromatography column
- washeluted with 30% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-7befaaf99ce442d5b793aa977f8c0803
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05240938
Reaction notes
Loading…