Cesium carbonate → HCID 59263329, compound

HRID 545887Notes

Reaction equation

HRID 545887 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:13]3=[CH:14][C:15]4[O:19][CH2:18][O:17][C:16]=4[CH:20]=[C:12]3[O:11][CH2:10]2)[C:2]1=[O:21].C([O-])([O-])=O.[Cs+].[Cs+].[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1>C(C(C)=O)C>[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]3([C:13]4=[CH:14][C:15]5[O:19][CH2:18][O:17][C:16]=5[CH:20]=[C:12]4[O:11][CH2:10]3)[C:2]2=[O:21])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Product 1

HCID 59263329HCID 59263329, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.16 g, 0.57 mmol) in ethylmethylketone (5.00 mL) was added Cs2CO3 (0.40 g, 1.20 mmol). The reaction mixture was stirred at ambient temperature for 15 min followed by the addition of 4-fluorobenzyl bromide (0.20 g, 1.0 mmol). The reaction mixture was refluxed for 4 h. After the completion of the reaction, the mixture was filtered and the solvent was removed under reduced pressure. The residue was recrystallized from EtOAc/Hexane to yield the title compound (0.111 g) as a white solid in 50% yield: MS (ES+) m/z 390.3 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. customAfter the completion of the reaction
  3. filtrationthe mixture was filtered
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was recrystallized from EtOAc/Hexane

Sources & evidence

ORD record
ord-93ec89fde54c49ab959749d8ce92faa9
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

Loading…