Triphenylphosphine → 6-[2-(1-Methyl-pyrrolidin-2-yl)-ethoxy]-quinoline-2-carboxylic acid ethyl ester

HRID 493428

Reaktionsgleichung

Reaktionsgleichung von HRID 493428
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:36][N:37]1[CH2:41][CH2:40][CH2:39][CH:38]1[CH2:42][CH2:43]O>C1(C)C=CC=CC=1.C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:43][CH2:42][CH:38]3[CH2:39][CH2:40][CH2:41][N:37]3[CH3:36])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 933631-Methyl-2-pyrrolidineethanolHCID 57681568Ethyl 6-hydroxyquinoline-2-carboxylate

Produkt 1

HCID 576815736-[2-(1-Methyl-pyrrolidin-2-yl)-ethoxy]-quinoline-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

A mixture of 0.400 g (0.002 mol) of 6-hydroxy-quinoline-2-carboxylic acid ethyl ester, 0.966 g (0.004 mmol) of triphenylphospine (Fluka), 0.396 g (0.003 mmol) of 1-methyl-2-pyrrolidineethanol and 0.68 ml (0.004 mmol) di-tert.-butyl azadicarboxylate 40% in toluene in 40 ml THF was stirred for a prolonged period of time at 35° C. The mixture was filtered through a pad of silica and washed with 30 ml THF. The mixture was evaporated to dryness and purified on silica eluting with a gradient of DCM/MeOH/NH4OH from 97/3/0.5 to 90/10/0.5. The ]

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of silica
  2. washwashed with 30 ml THF
  3. customThe mixture was evaporated to dryness
  4. custompurified on silica eluting with a gradient of DCM/MeOH/NH4OH from 97/3/0.5 to 90/10/0.5

Quellen und Nachweise

ORD-Eintrag
ord-7dc29766d7d545c8bee50288d1d87f5d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534891B2

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