Cesium carbonate → Methyl 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoate

HRID 1612435Notes

Reaction equation

HRID 1612435 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[C:6]([Br:11])[CH:5]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18].C([O-])([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]([Br:11])[CH:5]=1

Participants

7

Reactant 3

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

Product 1

HCID 22253055Methyl 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoateYield 82.4%

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
40 °C

Procedure

3-Bromo-5-iodobenzoic acid methyl ester (2.044 g, 5.996 mmol) in dioxane (25 ml) was treated with 2-pyrrolidinone (433 μl, 5.696 mmol), Cs2CO3 (2.93 g, 8.994 mmol), pd2(dba)3 (110 mg, 0.12 mmol) and Xantphos (208 mg, 0.36 mmol). The reaction mixture was heated to 40° C. for 3 days, then cooled to room temperature. The reaction mixture was filtered through celite and concentrated in vacuo. Column chromatography on silica gel (EtOAc) gave D9 (1.4 g) as a brown solid.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe reaction mixture was filtered through celite and
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3973de37196f4ebcb877a26826177032
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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