Morpholine → 4-{4-[4-(5-Bromo-pyridin-2-yl)-but-3-ynyl]-benzyl}-morpholine

HRID 271640

Reaktionsgleichung

CS(Cl)(=O)=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][CH:18]=2)=[N:11][CH:12]=1.C(N(C(C)C)C(C)C)C.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C(Cl)Cl>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:21][CH:22]=2)=[N:11][CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

36 μL (0.46 mmol) methanesulphonic acid chloride are added to a solution, cooled to 0° C., of 120 mg (0.38 mmol) {4-[4-(5-bromo-pyridin-2-yl)-but-3-ynyl]-phenyl}-methanol (Example 2.20a) in 5 mL DCM. A solution of 78 μL (0.46 mmol) ethyldiisopropylamine in 1 mL DCM is slowly added dropwise, the mixture is stirred for a further 30 min at 0° C., then 80 μL (0.92 mmol) of morpholine are added, the mixture is allowed to come up to RT and kept at RT for 2 h. The mixture is evaporated down i.vac., the residue is combined with 20 mL EtOAc and 10 mL water, acidified with 1 M HCl and the phases are separated. The aqueous phase is combined with 2 M Na2CO3 solution, extracted with 20 mL EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the product is obtained.

Aufarbeitung

customto come up to RT
waitkept at RT for 2 h
customThe mixture is evaporated down i.vac
customthe phases are separated
extractionextracted with 20 mL EtOAc
dry with materialthe organic phase is dried over Na2SO4
customis obtained

Quellen und Nachweise

ORD-Eintrag: ord-c8f8424bdfa542bcad375fc370055782
Quelldatensatz: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07452911B2

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