Potassium Carbonate → 1-Methylethyl 4-{[(6-bromo-2-fluoro-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate

HRID 423582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423582
[Br:1][C:2]1[N:7]=[C:6]([F:8])[C:5]([OH:9])=[CH:4][CH:3]=1.CS(O[CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([F:8])[C:5]([O:9][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 299198756-Bromo-2-fluoropyridin-3-olHCID 57930057Isopropyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylate

Produkt 1

HCID 866387411-Methylethyl 4-{[(6-bromo-2-fluoro-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Methylethyl 4-{[(6-bromo-2-fluoro-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (0.238 g, 68%) was prepared as a white solid from 6-bromo-2-fluoro-3-pyridinol (0.18 g, 0.94 mmol), 1-methylethyl 4-{[(methylsulfonyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 131, Step 4, 0.38 g, 1.22 mmol) and K2CO3 (0.26 g, 1.88 mmol) in DMF (10 mL) in a manner similar to Example 131, Step 5. The crude product was purified by flash chromatography on an ISCO silica gel column using 0 to 35% EtOAc/hexanes. 1H NMR (400 MHz, CDCl3): δ 7.27 (d, 1H, J=8.3 Hz), 7.20-7.10 (m, 1H), 4.91 (septet, 1H, J=6.2 Hz), 4.30-4.10 (m, 2H), 3.85 (d, 2H, J=6.3 Hz), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.75 (m, 2H), 1.45-1.20 (m, 8H); LRMS (ESI), m/z 375/377 (M+H).

Aufarbeitung

  1. customThe crude product was purified by flash chromatography on an ISCO silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-05612b188c454794affce493d80fe047
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101634B2

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