Sodium Carbonate → (1S,2R)-4'-[1-Ethyl-2-hydroxy-4-pyridin-3-yl-butoxyl]-4-fluorobiphenyl-3-sulfonic acid amide

HRID 380054

Reaktionsgleichung

Br[C:2]1[CH:28]=[CH:27][C:5]([O:6][C@@H:7]([CH2:25][CH3:26])[C@H:8]([O:17][Si](C(C)(C)C)(C)C)[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33](Br)=[CH:32][C:31]=1[S:37]([NH2:40])(=[O:39])=[O:38].C(=O)([O-])[O-].[Na+].[Na+]>C(O)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>[CH2:25]([C@@H:7]([C@H:8]([OH:17])[CH2:9][CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[O:6][C:5]1[CH:4]=[CH:3][C:2]([C:33]2[CH:34]=[CH:35][C:30]([F:29])=[C:31]([S:37]([NH2:40])(=[O:39])=[O:38])[CH:32]=2)=[CH:28][CH:27]=1)[CH3:26]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

Prepared according to the method described in Example 12b) from from (3R,4S)-3-[4-(4-Bromophenoxy)-3-(t-butyldimethylsilanyloxy)hexyl]pyridine (0.20 g, Example 88b)), 2-fluoro-5-bromophenylsulfonamide (0.177 g, Example 35a)), 2M aqueous sodium carbonate (0.54 ml) and tetrakis(triphenylphosphine)palladium (0) (0.014 g) in ethanol (3 ml) with heating at 90 ° C. for 4 hours. The residue was purified by column chromatography over silica eluting with ethyl acetate to give the title compound as a foam (0.14 g).

Aufarbeitung

customPrepared
customThe residue was purified by column chromatography over silica eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-0fca288079da4eb2aab0525a5ba69d35
Quelldatensatz: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06300352B1

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