Potassium Acetate → 7-Oxo-6,7-dihydro-5H-dibenzo[c,e]azepine-5-carboxylic Acid Methyl Ester

HRID 660572

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[CH:4]([NH:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1I)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1I.CC([O-])=O.[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]([CH:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13](=[O:21])[NH:12]1)=[O:22]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of (2-iodobenzoylamino)-(2-iodophenyl)-acetic acid methyl ester (3.4 g, 6.53 mmol) in DMF (300 mL) under argon is added PdCl2(dppf) (269 mg, 0.33 mmol) and KOAc (1.28 g, 13.06 mmol) and the mixture is heated at 110° C. for 18 h. Additional PdCl2(dppf) is added and heating is continued until all starting material is consumed. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 0-50% MeOH/methylene chloride as eluent to give the title compound as a yellow oil.

Workup

temperatureheating
customis consumed
customThe solvent is removed under reduced pressure
customthe residue purified by flash chromatography

Sources & evidence

ORD record: ord-f5e80b2965294fee9b2c92aaa0c2d7ed
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Linked notes

Loading…