Methyl 4-hydroxy-3-methoxyphenylacetate → Methyl 2-(3-methoxy-4-(4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yloxy)phenyl)acetate

HRID 2423310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423310
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][CH3:13])[CH:6]=1.[Na].Cl[C:17]1[C:18]([N+:34]([O-:36])=[O:35])=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:21]=[CH:20]2>C1COCC1>[CH3:13][O:12][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:14])[CH:10]=[CH:9][C:8]=1[O:11][C:17]1[C:18]([N+:34]([O-:36])=[O:35])=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:32])([CH3:33])[CH3:31])[N:21]=[CH:20]2

Komponenten

5

Edukt 3

HCID 85214Methyl 4-hydroxy-3-methoxyphenylacetateHCID 5360545SodiumHCID 598648595-chloro-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole

Produkt 1

HCID 59864798Methyl 2-(3-methoxy-4-(4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yloxy)phenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To methyl-3-methoxy-4-hydroxyphenylacetate (0.062 g, 0.32 mmol) in dry THF (5 mL) under nitrogen was added sodium hexamethyldisylazide (1M solution in THF) (312 μl, 0.31 mmol). After 10 min. stirring at room temperature 5-chloro-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (93 mg, 0.28 mmol) in 5 mL of THF was added. The resulting mixture was stirred at reflux for 5 days. After that time the mixture was quenched with water and extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The desired product was isolated by chromatography (10% ethyl acetate/hexane). 1H NMR (400 MHz) (CDCl3) δ 8.40 (s, 1H); 7.70 (d, J=9.1 Hz, 1H); 7.05 (d, J=9.1 Hz, 1H); 6.95 (m, 2H), 6.84 (dd, J=1.5, 8.0 Hz, 1H); 5.75 (s, 2H); 3.82 (s, 3H), 3.62, s, 3H); 3.62 (s, 2H); 3.57 (t, J=8.0 Hz, 2H); 0.89 (t, J=8.0 Hz, 2H); 0.0 (s, 9H).

Aufarbeitung

  1. additionwas added
  2. temperatureat reflux for 5 days
  3. customAfter that time the mixture was quenched with water
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-353d28c8e0194bc6a3ca81fd000ec45a
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960567B2

Notizen zur Reaktion

Wird geladen…