1-(Prop-2-yn-1-yl)piperidine → HCID 67157959, Verbindung

HRID 548554

Reaktionsgleichung

[CH2:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3].[CH3:10][O:11][C:12](=[O:34])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[C:24][C:25]2[CH:30]=[C:29]([Br:31])[CH:28]=[C:27](Br)[CH:26]=2)=[CH:17][C:16]=1[CH3:33]>CN(C=O)C.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>[CH3:10][O:11][C:12](=[O:34])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[C:24][C:25]2[CH:26]=[C:27]([C:3]#[C:2][CH2:1][N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)[CH:28]=[C:29]([Br:31])[CH:30]=2)=[CH:17][C:16]=1[CH3:33]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture of 1-prop-2-ynyl-piperidine (53 mg, 0.44 mmol), {4-[3-(3,5-dibromo-phenyl)-prop-2-ynyloxy]-2-methyl-phenoxy}-acetic acid methyl ester (204 mg, 0.44 mmol, intermediate 2), Pd(PPh3)4 (50 mg, 0.044 mmol), CuI (23 mg, 0.12 mmol) in dry DMF (2 ml) and triethylamine (2 ml) was heated in a microwave own for 30 min at 60° C. in a sealed tube. The reaction mixture was filtered through Decalite and the filtrate was evaporated. The residue was purified on column chromatography using ethyl acetate/methanol mixtures to give (4-{3-[3-bromo-5-(3-piperidin-1-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester in 105 mg (47%) yield.

Aufarbeitung

filtrationThe reaction mixture was filtered through Decalite
customthe filtrate was evaporated
customThe residue was purified on column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-c133269f32754ccf9df637f82283c00e
Quelldatensatz: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07943612B2

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