Dimethyl Sulfoxide → (R)-2-(5-Iodo-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 1625004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625004
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@H:13]([CH3:19])[CH2:14][O:15][C:16](=[O:18])[CH3:17])[C:7]2=[O:12].N([O-])=O.[Na+].CS(C)=O.[IH:28].C([O-])([O-])=O.[Na+].[Na+]>>[I:28][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@H:13]([CH3:19])[CH2:14][O:15][C:16](=[O:18])[CH3:17])[C:7]2=[O:12]

Komponenten

6

Edukt 5

HCID 679Dimethyl Sulfoxide2×HCID 10340Sodium CarbonateHCID 24841Hydrogen iodideHCID 23668193Sodium NitriteHCID 59515825(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Produkt 1

HCID 67203267(R)-2-(5-Iodo-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Versuchsvorschrift

Acetic acid (R)-2-(5-amino-1-oxo-1H-isoquinolin-2-yl)-propyl ester (790 mg, 0.0030 mol) was added to a solution of sodium nitrite (800 mg, 0.01 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) at room temperature. Aqueous hydrogen iodide (4 mL, 0.03 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) was added. The reaction mixture was stirred at room temperature for 1 hour. The cooled reaction mixture was neutralized with saturated aq. Na2CO3 and extracted with methylene chloride (3×100 mL). The combined methylene chloride extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was chromatographed on 40 of silica gel column (0-50% EtOAc/Hexane) to give the desired product as a brown oil. MS m/z (M+H) 371.9

Aufarbeitung

  1. customThe cooled reaction mixture
  2. extractionextracted with methylene chloride (3×100 mL)
  3. washThe combined methylene chloride extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was chromatographed on 40 of silica gel column (0-50% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1882d9c5f9fc480ba716ff280449d7bc
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08779144B2

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