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

HRID 852640Notes

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

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-bromo-5-iodobenzoic acid methyl ester (D8a) (588 mg, 1.72 mmol, 1.5 equiv) in dioxan (10 ml) was added pyrrolidin-2-one (120 μl, 1.14 mmol, 1 equiv), Cs2CO3 (720 mg, 2.21 mmol, 2 equiv), Xantphos (51 mg, 0.09 mmol, 0.08 equiv) and tris(dibenzylideneacetone)dipalladium (0) (28 mg, 0.03 mmol, 0.026 equiv). The reaction mixture was stirred at 100° C. for 16 h, then cooled to room temperature and filtered through a pad of celite and concentrated in vacuo. Purification by column chromatography on silica gel (EtOAc) yielded 3,5-bis-(2-oxo-pyrrolidin-1-yl)benzoic acid methyl ester (B24) (411 mg, 79%) as light yellow solid. [M+H]+=303.2

Workup

temperaturecooled to room temperature
filtrationfiltered through a pad of celite
concentrationconcentrated in vacuo
customPurification by column chromatography on silica gel (EtOAc)

Sources & evidence

ORD record: ord-ac2b2fd536d54a398ebd80f4f4cbf6c0
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

Loading…