Sodium Carbonate → HCID 86715485, Verbindung

HRID 2284576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2284576
[Cl:1][C:2]1[C:7]([C:8]2[CH:16]=C[C:11]3[N:12]=[CH:13]S[C:10]=3[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.BrC1C=CC2[N:22]([N:24]=CN=2)C=1.ClC1C(B2OC(C)(C)C(C)(C)O2)=CC=CN=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C(Cl)Cl.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:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]3[N:22]([N:24]=[CH:13][N:12]=3)[CH:16]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 115139346-Bromo-[1,2,4]triazolo[1,5-a]pyridineHCID 120670602-Chloropyridine-3-boronic acid pinacol esterHCID 867154766-(2-Chloropyridin-3-yl)benzo[d]thiazole

Produkt 1

HCID 86715485HCID 86715485, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

6-(2-Chloropyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine was synthesized in the similar to 6-(2-chloropyridin-3-yl)benzo[d]thiazole from 6-bromo[1,2,4]triazolo[1,5-a]pyridine (1.0 g, 5.0 mmol), 2-chloro-3-pyridine boronic acid pinacol ester (1.45 g, 6.0 mmol), Pd(PPh3)4 (300 mg, 0.26 mmol) and 2M aq.Na2CO3 (8 mL, 16 mmol) in 1,4-dioxane (50 mL). Upon workup, the crude residue was dissolved in CH2Cl2 (10 mL) and stirred with 50% EtOAc/hexanes (40 mL). The resulting off-white precipitate was filtered and dried to provide 6-(2-chloropyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine (0.68 g, 58%). 1H NMR (DMSO-d6): δ 9.18 (dd, 1H, J=0.86 and 1.7 Hz), 8.57 (s, 1H), 8.50 (dd, 1H, J=1.7 and 4.9 Hz), 8.05 (dd, 1H, J=2.0 and 7.8 Hz), 7.94 (dd, 1H, J=0.9 and 9.1 Hz), 7.80 (dd, 1H, J=1.7 and 9.1 Hz), 7.59 (dd, 1H, J=4.7 and 7.6 Hz).LCMS: rt 5.00 min (A), purity 97%, MS (m/e) 231.

Aufarbeitung

  1. filtrationThe resulting off-white precipitate was filtered
  2. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c0a9d5f36e8a43eb912a492784954b0c
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145433B2

Notizen zur Reaktion

Wird geladen…