Triphenylphosphine → 4-Chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)cinnoline

HRID 2180118

Reaktionsgleichung

Reaktionsgleichung von HRID 2180118
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:34]1([CH2:39][CH2:40][CH2:41]O)[CH2:38][CH2:37][CH2:36][CH2:35]1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:41][CH2:40][CH2:39][N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 2093421-PyrrolidinepropanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1357525234-Chloro-7-hydroxy-6-methoxycinnoline

Produkt 1

HCID 112786904-Chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)cinnolineAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-7-hydroxy-6-methoxycinnoline (300 mg, 1.42 mmol), triphenylphosphine (747 mg, 2.85 mmol) and 3-(pyrrolidin-1-yl)propan-1-ol (276 mg, 2.1 mmol) in methylene chloride (12 ml) was added diethyl azodicarboxylate (449 μl, 2.85 mmol) dropwise and the mixture was stirred for 2 hours at ambient temperature. The volatiles were removed under vacuum and the residue was purified by column chromatography eluting with methylene chloride/methanol (90/10) followed by methylene chloride/methanol/methanol saturated with ammonia (89/10/1 followed by 85/10/5). The fractions containing the expected product were combined and evaporated to give 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)cinnoline (80 mg, 18%).

Aufarbeitung

  1. customThe volatiles were removed under vacuum
  2. customthe residue was purified by column chromatography
  3. washeluting with methylene chloride/methanol (90/10)
  4. additionThe fractions containing the expected product
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-69bbf242a4eb4472863103edf67ac4cc
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06887874B2

Verknüpfte Notizen

Wird geladen…