Dichloromethane → 4-[2-(3-Pyridyl)ethenyl]-2-phenylbenzoic Acid Methyl Ester

HRID 2121225Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:18]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)=[CH2:19].ClCCl.C(N(CC)CC)C>CN1CCCC1=O.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](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH:19]=[CH:18][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the 4-iodo-2-phenylbenzoic acid methyl ester (6.11 g, 18.1 mmol), prepared as in Example 210C, 3-vinylpyridine (2.85 g, 27.1 mmol), prepared as in Example 210E, [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complexed to dichloromethane (1:1) (444 mg, 0.543 mmol) and triethylamine (5.05 g, 36.2 mmol), in 1-methyl-2-pyrrolidinone (30 mL) was degassed with nitrogen and heated at 80° C. for 18 hours. The reaction mixture was diluted with ether, filtered through silica gel, and rinsed with ethyl acetate. The filtrate was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (30% ethyl acetate-hexane) to give the title compound (4.82 g, 84%).

Workup

customwas degassed with nitrogen
additionThe reaction mixture was diluted with ether
filtrationfiltered through silica gel
washrinsed with ethyl acetate
washThe filtrate was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (30% ethyl acetate-hexane)

Sources & evidence

ORD record: ord-83f91f8c70494eae9e6968ad95c5bbbc
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693123B2

Reaction notes

Loading…