Methyl iodide → Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate

HRID 2283473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2283473
[OH:1][C:2]1[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]([I:19])=[CH:4][N:3]=1.[CH3:20]I>C(Cl)(Cl)Cl>[I:19][C:5]1[CH:6]=[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]([O:1][CH3:20])=[N:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 178522276HCID 178522276, Verbindung

Produkt 1

HCID 59432848Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamateAusbeute 53,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of benzyl (2-hydroxy-5-iodopyridin-3-yl)carbamate (16 g, 43 mmol) in CHCl3 (250 mL) was added Ag2CO3 (16.1 g, 58.4 g) and methyl iodide (27.0 mL, 434 mmol) in the dark, and the mixture stirred at RT for overnight. The solid was removed by filtration and the solvent was concentrated and purified by combi-flash (ISCO, 40g silica, UV254, 5:1 pet ether/ethyl acetate) to afford benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate (8.85 g, 53% yield) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.61 (br, 1H), 7.98 (d, J=1.6 Hz, 1H), 7.35-7.42 (m, 5H), 7.12 (s, 1H), 5.21 (s, 2H), 3.95 (s, 3H); MS (ES) m/z 385 (M+H).

Aufarbeitung

  1. customThe solid was removed by filtration
  2. concentrationthe solvent was concentrated
  3. custompurified by combi-flash (ISCO, 40g silica, UV254, 5:1 pet ether/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-954555dc8a2c48878e91d4c82f3d31e9
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145393B2

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