(+/-) Methyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-3-ethynylpropionate → HCID 53907478, compound

HRID 1637102Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:9]=1)[C:6]#[CH:7].I[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[O:31][C:32]([CH3:35])=[N:33][N:34]=2)[CH:25]=1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:9]=1)[C:6]#[C:7][C:28]1[CH:29]=[CH:24][CH:25]=[C:26]([C:30]2[O:31][C:32]([CH3:35])=[N:33][N:34]=2)[CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the compound from Example 7 (0.15 g, 0.5 mmol) and 1-iodo-3-(5-methyl-[1,3,4]oxadiazol-2-yl)benzene (0.14 g, 0.5 mmol) in triethylamine (5 mL) under an argon atmosphere was added trace tetrakis(triphenylphosphine)palladium(0) and trace copper(I) iodide. The mixture was heated at 80° C. for 0.2 h, was cooled to room temperature and was concentrated in vacuo. Purification by flash chromatography (silica gel, 50% EtOAc/hexane) provided the titled compound as a yellow oil (0.19 g, 80%). Anal. (C27H28N2O5· 0·375 H2O) calcd: C, 69.40; H, 6.20; N, 6.00. found: C, 69.23; H, 6.13;N,5.69.

Workup

temperaturewas cooled to room temperature
concentrationwas concentrated in vacuo
customPurification by flash chromatography (silica gel, 50% EtOAc/hexane)

Sources & evidence

ORD record: ord-428cdb6cae7244ab932aa3b46becba8f
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06037367

Reaction notes

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