Hydrochloric Acid → HCID 59326606, Verbindung

HRID 238615Notizen

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[C:6]=1[F:17].Br[C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[C:6]=1[F:17]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A mixture of (1,6-difluoro-4-hydroxy-naphthalen-2-yl)acetic acid methyl ester (50 mg, 0.198 mmol), 2-bromo-5-methanesulfonyl-pyridin (52 mg, 0.22 mmol), potassium carbonate (60 mg, 0.434 mmol) and N,N-dimethylformamide (2.0 mL) was heated at 70° C. for 3 hours. The resulting mixture was cooled to room temperature, acidified with 1 N hydrochloric acid to pH 3, and extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with brine (20 mL×3), dried over sodium sulfate, and concentrated in vacuo to afford [1,6-difluoro-4-(5-methanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-acetic acid methyl ester (70 mg, 87%) as a white solid which was used in the next step without further purification.

Aufarbeitung

temperatureThe resulting mixture was cooled to room temperature
extractionextracted with ethyl acetate (20 mL×3)
washThe combined organic layers were washed with brine (20 mL×3)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-e78e969d08a04a4983a672d7fa8f5f4b
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08642629B2

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