Sodium Carbonate → 5-(2-Oxopyrrolidin-1-yl)-biphenyl-3-carboxylic Acid Methyl Ester

HRID 1612436Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6](Br)[CH:5]=1.C([O-])([O-])=O.[Na+].[Na+].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>COCCOC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:9]=1)=[O:17]

Participants

Conditions

Temperature: 85 °C

Procedure

To 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoic acid methyl ester (D9) (70 mg, 0.235 mmol) in DME (2 ml) was added Na2CO3 (290 μl, 2M, 0.588 mmol), benzeneboronic acid (29 mg, 0.235 mmol) and Pd(OAc)2 (3 mg, 0.013 mmol). The mixture was stirred at 85° C. for 2 days. The reaction mixture was cooled down, filtrated through celite and evaporated in vacuo. The product was purified by column chromatography (PE:EtOAc=3:1) which yielded D10 (23 mg).

Workup

temperatureThe reaction mixture was cooled down
filtrationfiltrated through celite
customevaporated in vacuo
customThe product was purified by column chromatography (PE:EtOAc=3:1) which

Sources & evidence

ORD record: ord-95a34c1f03144faaa63971fadbafdd6d
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06992103B2

Reaction notes

Loading…