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Sodium Carbonate → 7-[2-Chloro-3-(trifluoromethyl)benzyl]-3-(4-fluorophenyl)-6,7-dihydro[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one

HRID 576711
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 576711
Br[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=3[Cl:23])[C:10](=[O:11])[C:5]2=[N:4][N:3]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>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>[Cl:23][C:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][N:9]1[CH2:8][CH2:7][N:6]2[C:2]([C:28]3[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=3)=[N:3][N:4]=[C:5]2[C:10]1=[O:11]
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Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 904024003-bromo-7-(2-chloro-3-(trifluoromethyl)benzyl)-6,7-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one

Produkt 1

HCID 862792227-[2-Chloro-3-(trifluoromethyl)benzyl]-3-(4-fluorophenyl)-6,7-dihydro[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-oneAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-bromo-7-(2-chloro-3-(trifluoromethyl)benzyl)-6,7-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one (100 mg, 0.24 mmol) and 4-fluorophenylboronic acid (40 mg, 0.27 mmol) in dioxane (0.6 mL) was added 1M Na2CO3 (0.6 mL). The flask was purged with nitrogen for 10 minutes and Pd(PPh3)4 (14 mg, 0.012 mmol) was added at once. The flask was purged with nitrogen for an additional 5 minutes and then heated at 100° C. for 18 h. After cooling to rt, brine was added, and the mixture was extracted with EtOAc (×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to give a brown solid. Purification by chromatography (SiO2; hexanes—100% EtOAc) afforded the desired product as a white solid (47 mg, 45%). MS (ESI): mass calcd. for C19H13ClF4N4O, 424.1; m/z found, 425.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 7.91-7.73 (m, 4H), 7.59-7.54 (m, 1H), 7.49-7.43 (m, 2H), 4.89 (s, 2H), 4.56-4.42 (m, 2H), 3.92-3.84 (m, 2H).

Aufarbeitung

  1. customThe flask was purged with nitrogen for 10 minutes
  2. customThe flask was purged with nitrogen for an additional 5 minutes
  3. temperatureAfter cooling to rt
  4. additionbrine was added
  5. extractionthe mixture was extracted with EtOAc (×3)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown solid
  10. customPurification by chromatography (SiO2; hexanes—100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-fa67533ec23c48ee81ab84485ecc0460
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040534B2

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