Boron tribromide → 2-[3-(3-chlorophenyl)-7-hydroxy-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide

HRID 602280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602280
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH2:21][C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[C:10](=[O:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[C:13]([O:18]C)[CH:12]=3)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH2:21][C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[C:10](=[O:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[C:13]([OH:18])[CH:12]=3)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 596842522-[3-(3-chlorophenyl)-7-methoxy-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide

Produkt 1

HCID 596842412-[3-(3-chlorophenyl)-7-hydroxy-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamideAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2-[3-(3-chlorophenyl)-7-methoxy-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide (886 mg, 2.30 mmol) in dry DCM (25 mL) was cooled to −78° C. and a solution of BBr3 (1 M in DCM, 20.3 mL, 20.3 mmol) was added dropwise. After 1 h, the cooling bath was removed and the mixture was allowed to stir an additional 17.5 h, then cooled to 0° C. and quenched by dropwise addition of sat. NaHCO3 (aq.) (15 mL). The aqueous mixture was extracted with IPA:DCM (1:3, v/v) (4×25 mL). The combined organic extracts were washed with brine (25 mL), dried (MgSO4) and concentrated to give the crude product, which was recrystallized from EtOH to give pure 2-[3-(3-chlorophenyl)-7-hydroxy-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide (INTERMEDIATE III.7) (530 mg, 1.43 mmol, 62%) as white solid.

Aufarbeitung

  1. customthe cooling bath was removed
  2. customquenched by dropwise addition of sat. NaHCO3 (aq.) (15 mL)
  3. extractionThe aqueous mixture was extracted with IPA:DCM (1:3
  4. washThe combined organic extracts were washed with brine (25 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas recrystallized from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-acd1c3bd998d4316bf42cc3b9631ff24
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906504B2

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