Cesium carbonate → 3,5-Bis-(2-oxo-pyrrolidin-1-yl)benzoic Acid Methyl Ester

HRID 1612433Notes

Reaction equation

HRID 1612433 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[C:6](Br)[CH:5]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18].[C:19]([O-:22])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:7]=[C:6]([N:13]2[CH2:14][CH2:15][CH2:16][C:19]2=[O:22])[CH:5]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 21942573Methyl 3-bromo-5-iodobenzoate

Product 1

HCID 693577583,5-Bis-(2-oxo-pyrrolidin-1-yl)benzoic Acid Methyl EsterYield 238.5%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-bromo-5-iodobenzoic acid methyl ester (588 mg, 1.72 mmol) in dioxane (10 ml) was added 2-pyrrolidinone (120 μl, 1.14 mmol), Cs2CO3 (720 mg, 2.21 mmol), xantphos (51 mg, 0.09 mmol) and pd2(dba)3 (28 mg, 0.03 mmol). The reaction mixture was stirred at 100° C. overnight, then cooled down to room temperature and filtered through celite and concentrated in vacuo. The product was purified by column chromatography (EtOAc) which yielded D7 (411 mg) as light yellow solid.

Workup

  1. temperaturecooled down to room temperature
  2. filtrationfiltered through celite and
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by column chromatography (EtOAc) which

Sources & evidence

ORD record
ord-571ffa9281904ae49e27b3047906d727
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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