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Potassium Carbonate → 3-(5-Chloro-8-fluoroisoquinolin-3-yl)-5-thiophen-3-ylpyridin-2-amine

HRID 1926323
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1926323
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[CH:11][C:12]3[C:17]([CH:18]=2)=[C:16]([Cl:19])[CH:15]=[CH:14][C:13]=3[F:20])[C:5]([NH2:8])=[N:6][CH:7]=1.[S:21]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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]>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([F:20])=[C:12]2[C:17]=1[CH:18]=[C:9]([C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:23]3[CH:24]=[CH:25][S:21][CH:22]=3)[CH:3]=1)[N:10]=[CH:11]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 675207675-Bromo-3-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-2-ylamine

Produkt 1

HCID 675212113-(5-Chloro-8-fluoroisoquinolin-3-yl)-5-thiophen-3-ylpyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 5-bromo-3-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-2-ylamine (BB4) (25 mg, 0.070 mmol), 3-thienylboronic acid (20 mg, 0.10 mmol) and potassium carbonate (29 mg, 0.21 mmol) in 1,4-dioxane (1.0 mL) and H2O (0.4 mL) was degassed and refilled with argon (3×) prior to the addition of Pd(dppf)Cl2 (5 mg, 0.01 mmol). The reaction mixture was degassed and refilled with argon (2×) and left to stir at 100° C. in the microwave reactor for 30 min. Then, the mixture was passed through PL-Thiol MP SPE resin and concentrated in vacuo. The residual oil was partitioned between DCM and H2O. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification via MDP afforded the title compound as a yellow solid. MS (ES+): m/z=356.03/358.05 (100/50) [MH+]. HPLC: tR=3.22 min (ZQ2, polar—5 min).

Aufarbeitung

  1. customwas degassed
  2. additionrefilled with argon (3×)
  3. customThe reaction mixture was degassed
  4. additionrefilled with argon (2×)
  5. waitleft
  6. concentrationconcentrated in vacuo
  7. customThe residual oil was partitioned between DCM and H2O
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customPurification via MDP

Quellen und Nachweise

ORD-Eintrag
ord-55a3989c98b049eeb61436478f1f8992
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08178668B2

Notizen zur Reaktion

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