Potassium Carbonate → 2-(3-bromo-2-methylphenyl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 1811064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811064
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9].[C:10]1(=[O:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][NH:11]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(Cl)Cl.[Cu]I>[Br:8][C:4]1[C:3]([CH3:9])=[C:2]([N:11]2[CH2:12][CH2:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]2=[O:20])[CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 346812,6-Dibromotoluene2×HCID 1508963,4-dihydroisoquinolin-1(2H)-one2×

Produkt 1

HCID 593751142-(3-bromo-2-methylphenyl)-3,4-dihydroisoquinolin-1(2H)-oneAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Step 2 A mixture of 1,3-dibromo-2-methylbenzene (340 mg, 1.359 mmol), 3,4-dihydroisoquinolin-1(2H)-one (100 mg, 0.679 mmol) and potassium carbonate (94 mg, 0.679 mmol) in DMSO (2 mL) was purged with nitrogen, treated with copper (I) iodide (25.9 mg, 0.136 mmol) and heated at 150° C. for 3.5 h. The mixture was combined with that from a second reaction using 1,3-dibromo-2-methylbenzene (2.59 g, 10.36 mmol) and 3,4-dihydroisoquinolin-1(2H)-one (508 mg, 3.45 mmol), diluted with DCM and filtered through Celite. The filtrate was washed with 5% aqueous ammonium hydroxide, dried and concentrated. The residue was purified by column chromatography (eluting with hexane-EtOAc) to provide 2-(3-bromo-2-methylphenyl)-3,4-dihydroisoquinolin-1(2H)-one as a yellow solid (142 mg, 11%). 1H NMR (400 MHz, chloroform-d) δ 8.15 (1H, dd, J=7.70, 1.10 Hz), 7.55 (1H, dd, J=7.92, 1.10 Hz), 7.46-7.51 (1H, m), 7.37-7.42 (1H, m), 7.24-7.28 (1H, m), 7.17-7.21 (1H, m), 7.09-7.16 (1H, m), 3.95 (1H, ddd, J=12.21, 10.12, 4.73 Hz), 3.73 (1 H, ddd, J=11.94, 6.33, 5.28 Hz), 3.26 (1H, ddd, J=15.74, 10.23, 5.28 Hz), 3.06-3.14 (1H, m), 2.36 (3H, s). Mass spectrum m/z 316, 318 (M+H)+.

Aufarbeitung

  1. customwas purged with nitrogen
  2. customfrom a second reaction
  3. filtrationfiltered through Celite
  4. washThe filtrate was washed with 5% aqueous ammonium hydroxide
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (eluting with hexane-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-36da27590a8d49a888e56c77464559eb
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362065B2

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