Iodide Ion → HCID 67483971, compound

HRID 1936268Notes

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:22]=[N:23][CH:24]=[N:25][CH:26]=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:22]=[N:23][CH:24]=[N:25][CH:26]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (719 mg, 2.01 mmol) and triethylamine (3 mL, 0.015 mmol) in N,N-dimethylformamide (3 mL) was treated with 5-ethynyl-pyrimidine (230 mg, 2.21 mmol). The resulting reaction mixture was degassed with argon for 10 min and then treated with cooper iodide (92 mg, 0.48 mmol) and bis(triphenylphosphine)palladium (II) chloride (169 mg, 0.24 mmol). The reaction was stirred at 25° C. for 18 h and then heated at 67° C. for 2 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-pyrimidin-5-ylethynyl-phenyl)-propionic acid methyl ester (440 mg, 66%) as an orange oil: EI-HRMS m/e calcd for C21H22N2O2 (M+) 334.1681, found 334.1681.

Workup

customThe resulting reaction mixture
customwas degassed with argon for 10 min
temperatureheated at 67° C. for 2 h
temperatureAt this time, the reaction was cooled to 25° C.
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b88a8aedf93346448d167ff5232bfe77
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06388071B2

Reaction notes

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