Pyridine → 2-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]phenyl}ethyl methanesulfonate

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Reaktionsgleichung

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][OH:29])=[CH:23][CH:22]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1.N1C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:29][CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]#[C:19][C:16]2[CH:15]=[CH:14][C:13]([C:10]3[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=3)=[CH:18][N:17]=2)=[CH:26][CH:25]=1)(=[O:4])=[O:3]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

0.06 mL (0.75 mmol) of methanesulfonic acid chloride was added dropwise at 0° C. to a solution of 167 mg (0.50 mmol) of 2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenyl}ethanol and 0.08 mL (1.00 mmol) of pyridine in 5 mL of DCM and the mixture was then stirred for I hour at 0° C. It was combined again with pyridine (0.08 mL) and methanesulfonic acid chloride (0.06 mL) and stirred for 1 hour at RT. Then it was combined with 0.14 mL (1.00 mmol) of triethylamine and after 20 minutes at RT diluted with ice water. The organic phase was separated off, dried over magnesium sulfate, filtered, and the solvent was eliminated in vacuo. Yield: 185 mg (90% of theoretical); C22H18ClNO3S (M=411.902); calc.: molpeak (M+H)+:412/414 (Cl); found: molpeak (M+H)+:412/414 (Cl); HPLC-MS: 6.27 minutes (method H).

Aufarbeitung

stirringstirred for 1 hour at RT
customThe organic phase was separated off
dry with materialdried over magnesium sulfate
filtrationfiltered
custom6.27 minutes (method H)

Quellen und Nachweise

ORD-Eintrag: ord-562e00ed531d451f93b4ee974bbba072
Quelldatensatz: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07592358B2

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