Diethyl Ether → HCID 19041710, compound

HRID 1684011Notes

Reaction equation

HRID 1684011 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17].[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1.[H-].[Na+].CCOCC>CN(C=O)C>[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([O:18][CH3:19])=[O:17])=[C:7]2[CH3:12])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 19041638HCID 19041638, compound

Product 1

HCID 19041710HCID 19041710, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. mixture of the indole from Step 3 (285 mg, 0.96 mmol) and 4-bromobenzyl bromide (310 mg, 1.05 mmol) in DMF (5 mL) was added NaH (44 mg, 1.1 mmol). The mixture was warmed up to r.t. and stirred for 1.5 h after which time it was poured on a mixture of ice water and Et2O. The organic layer was washed with brine, dried with MgSO4 and the solvent removed to yield a residue which was used as such in the next step.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried with MgSO4
  3. customthe solvent removed
  4. customto yield a residue which

Sources & evidence

ORD record
ord-33357345ad0047f8b2e98bd3c4e92416
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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