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Sodium Carbonate → 6-Cyclopropyl-7-(5-fluoropyridin-3-yl)-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

HRID 1521668
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1521668
Br[C:2]1[C:3]([CH:16]2[CH2:18][CH2:17]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([CH3:15])=[N:13][N:14]=[C:7]1[CH2:6][CH2:5]2.[F:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[N:24][CH:25]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH:16]1([C:3]2[C:2]([C:22]3[CH:23]=[N:24][CH:25]=[C:20]([F:19])[CH:21]=3)=[CH:11][CH:10]=[C:9]3[C:4]=2[CH2:5][CH2:6][C:7]2[N:8]3[C:12]([CH3:15])=[N:13][N:14]=2)[CH2:18][CH2:17]1
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Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 709779917-Bromo-6-cyclopropyl-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

Produkt 1

HCID 899617136-Cyclopropyl-7-(5-fluoropyridin-3-yl)-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 7-bromo-6-cyclopropyl-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline (147-8; 0.250 g, 0.00082 mol) and (5-fluoropyridin-3-yl)boronic acid (0.126 g, 0.009 mol) in the mixture of 1,4-dioxane (10 mL) and water (10 mL) was added sodium carbonate (0.260 g, 0.00246 mol). Reaction mass was purged with argon for 20 min. Then catalyst Pd(dppf)2Cl2 (0.066 g, 0.000082 mol) was added and allowed to stir at 80° C. for 12 h. The reaction mixture was filtered through CELITE bed and filter bed was thoroughly washed with ethyl acetate. The collected organic layer was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.587-8.580 (d, J=2.8 Hz, 1H), 8.548 (s, 1H), 7.881-7.856 (d, J=10 Hz, 1H), 7.679-7.658 (d, J=8.4 Hz, 1H), 7.401-7.380 (d, J 8.4 Hz, 1H), 3.237-3.203 (t, J=6.8 Hz, 2H), 3.050-3.016 (t, J=7.2 Hz, 2H), 2.671 (s, 3H), 2.175 (s, 1H), 0.759-0739 (d, J 8 Hz, 2H), 0.034-0.022 (d, J=4.8 Hz, 2H), MS (M+1): 321.2.

Aufarbeitung

  1. customReaction mass
  2. customwas purged with argon for 20 min
  3. filtrationThe reaction mixture was filtered through CELITE bed
  4. filtrationfilter bed
  5. washwas thoroughly washed with ethyl acetate
  6. concentrationThe collected organic layer was concentrated under vacuum
  7. customto afford the crude compound, which
  8. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2634feb02a74447f9c4bc63faa675067
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09073929B2

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