Methanol → 2,2,2-Trifluoro-1-{6-hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl}ethanone

HRID 397074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397074
B(Br)(Br)Br.[F:5][C:6]([F:36])([F:35])[C:7]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19]C)[CH:15]=2)[CH:10]1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:23][CH:22]=1)=[O:8].CO>C(Cl)Cl>[F:35][C:6]([F:5])([F:36])[C:7]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[CH:10]1[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]2[CH2:31][CH2:32][CH2:33][CH2:34]2)=[CH:25][CH:26]=1)=[O:8]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 25134Boron tribromideHCID 120859402,2,2-Trifluoro-1-{6-methoxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl}ethanone

Produkt 1

HCID 120859412,2,2-Trifluoro-1-{6-hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl}ethanoneAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 1M solution of BBr3 in CH2Cl2 (35.0 ml, 35.0 mmol) was added slowly to a solution of 2,2,2-trifluoro-1-{6-methoxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl}ethanone (6.26 g, 14.0 mmol) in anhydrous CH2Cl2 (400 ml) at 0° C. under N2. The reaction mixture was warmed to rt and stirred at rt for 21 hr. MeOH (100 ml) was slowly added with stirring and the resulting solution was concentrated in vacuo to a red oil. Purification by flash chromatography, eluting with EtOAc:MeOH (8:2), gave 1.886 g (31% yield) of yellow solid.

Aufarbeitung

  1. stirringwith stirring
  2. concentrationthe resulting solution was concentrated in vacuo to a red oil
  3. customPurification by flash chromatography
  4. washeluting with EtOAc:MeOH (8:2)

Quellen und Nachweise

ORD-Eintrag
ord-b27d93941b3146bbab00cc74f8f24934
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608203B2

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