HCID 19349925, compound → HCID 54557479, compound

HRID 1637120Notes

Reaction equation

[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:19]#[CH:20])[CH2:16][CH:17]=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[N:32]=[C:31]([CH3:33])[O:30][N:29]=2)[CH:23]=1>C(N(CC)CC)C.[Cu]I>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:19]#[C:20][C:26]3[CH:27]=[CH:22][CH:23]=[C:24]([C:28]4[N:32]=[C:31]([CH3:33])[O:30][N:29]=4)[CH:25]=3)[CH2:16][CH:17]=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)pent-4-ynal (0.20 g, 0.73 mmol) and 1-iodo-3-(5-methyl-[1,2,4]oxadiazol-3-yl)benzene (0.21 g, 0.73 mmol) and trace tetrakistriphenylphosphine palladium (0) and trace copper(I)iodide in triethylamine (5 mL)under an argon atmosphere was heated at 80° C. for 0.25 h. The mixture was cooled to room temperature and was evaporated. The residue was purified by flash chromatography (silica gel, 35% EtOAc/Hex) to provide the title compound as a yellow oil (0.22 g, 71%).1H NMR (250 Mhz, CDCl3) δ 9.86 (t, J=1.7 Hz, 1 H), 8.15, (d, J=1.4 Hz, 1 H), 8.01 (dt, J=7.8 and 1.4 Hz, 1 H), 7.54 (dt, J=7.8 and 1.4 Hz, 1 H), 7.42 (t, J=7.8 Hz),lH), 6.95 (m. 2 H), 6.84 (d, J=8.5 Hz, 1 H), 4.8 (m, 1 H), 4.40 (t, J=7 Hz, 1 H), 3.85 (s, 3 H), 2.86-3.10 (m, 2 H), 2.66 (s, 3 H), 1.80-2.05 (m, 6 H), 1.60-1.69 (m, 2 H).

Workup

temperatureThe mixture was cooled to room temperature
customwas evaporated
customThe residue was purified by flash chromatography (silica gel, 35% EtOAc/Hex)

Sources & evidence

ORD record: ord-396b962fab7d476b8db2c7bcaedb7458
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06037367

Reaction notes

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