Iodide Ion → 3-Cyclopentyl-2-(4-pyridin-2-ylethynyl-phenyl)-propionic acid methyl ester

HRID 1936263Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)#[CH:20].[I-]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:20]#[C:19][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (1.0 g, 2.79 mmol) and triethylamine (4 mL, 0.02 mmol) in N,N-dimethylformamide (4 mL) was treated with 2-ethynylpyridine (345 mg, 3.34 mmol). The resulting reaction mixture was degassed with argon for 10 min and then treated with cooper iodide (168 mg, 0.88 mmol) and bis(triphenylphosphine)palladium (II) chloride (305 mg, 0.44 mmol). The reaction was then heated at 70° C. for 1.5 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-pyridin-2-ylethynyl-phenyl)-propionic acid methyl ester (900 mg, 97%) as a yellow oil: EI-HRMS m/e calcd for C22H23NO2 (M+) 333.1728, found 333.1724.

Workup

customThe resulting reaction mixture
customwas degassed with argon for 10 min
temperatureAt this time, the reaction was cooled to 25° C.
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-104b477a7aae429dbd53e7f6fe6294af
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06388071B2

Reaction notes

Loading…