6-(2-amino-5-bromopyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one → 6'-amino-N-ethyl-N-methyl-5'-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-[2,3'-bipyridine]-5-sulfonamide

HRID 2091560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091560
[CH2:1]([N:3]([CH3:17])[S:4]([C:7]1[CH:8]=[N:9][C:10]([Sn](C)(C)C)=[CH:11][CH:12]=1)(=[O:6])=[O:5])[CH3:2].[NH2:18][C:19]1[C:24]([C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[C:31](=[O:35])[NH:30][CH2:29][CH2:28]3)=[CH:23][C:22](Br)=[CH:21][N:20]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:18][C:19]1[N:20]=[CH:21][C:22]([C:10]2[CH:11]=[CH:12][C:7]([S:4]([N:3]([CH2:1][CH3:2])[CH3:17])(=[O:6])=[O:5])=[CH:8][N:9]=2)=[CH:23][C:24]=1[C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31](=[O:35])[NH:30][CH2:29][CH2:28]2

Komponenten

5

Edukt 2

HCID 682933526-(2-amino-5-bromopyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-oneHCID 70655349N-ethyl-N-methyl-6-(trimethylstannyl)pyridine-3-sulfonamide

Produkt 1

HCID 706547986'-amino-N-ethyl-N-methyl-5'-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-[2,3'-bipyridine]-5-sulfonamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of N-ethyl-N-methyl-6-(trimethylstannyl)pyridine-3-sulfonamide (225 mg, 0.6 mmol) and 6-(2-amino-5-bromopyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (190 mg, 0.6 mmol) and Pd(PPh3)4 (34 mg, 0.03 mmol) in dioxane (3 mL) was degassed and heated to 90° C. At completion, the reaction was cooled to room temperature and concentrated. The residue was purified by flash chromatography over silica gel to provide 6′-amino-N-ethyl-N-methyl-5′-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-[2,3′-bipyridine]-5-sulfonamide as a yellow solid (134 mg, 50% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.88 (dd, J=17.9, 2.1 Hz, 2H), 8.17-8.22 (m, 1H), 8.10-8.16 (m, 2H), 7.94 (d, J=7.8 Hz, 2H), 7.43-7.51 (m, 2H), 3.41 (s, 2H), 3.30 (s, 3H), 2.97 (t, J=6.4 Hz, 2H), 0.86 (t, J=7.3 Hz, 3H); MS (EI) m/z=438.5 [M+1]+.

Aufarbeitung

  1. customwas degassed
  2. temperatureAt completion, the reaction was cooled to room temperature
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8b4a1cb971ea44468a05552512d118b0
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440652B2

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