Sodium Carbonate → HCID 86715477, Verbindung

HRID 2284569

Reaktionsgleichung

Reaktionsgleichung von HRID 2284569
[Cl:1][C:2]1[C:7]([C:8]2[CH:16]=[CH:15][C:11]3N=CS[C:10]=3[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.BrC1C=CC2[S:25][CH:24]=[N:23]C=2C=1.ClC1C(B2OC(C)(C)C(C)(C)O2)=CC=CN=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:1][C:2]1[C:7]([C:8]2[CH:16]=[CH:15][C:11]3[S:25][CH:24]=[N:23][C:10]=3[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 36101555-BromobenzothiazoleHCID 120670602-Chloropyridine-3-boronic acid pinacol esterHCID 867154766-(2-Chloropyridin-3-yl)benzo[d]thiazole

Produkt 1

HCID 86715477HCID 86715477, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

5-(2-chloropyridin-3-yl)benzo[d]thiazole was prepared in the similar manner of 6-(2-chloropyridin-3-yl)benzo[d]thiazole by heating the mixture of 5-bromobenzothiazole (1.0 g, 4.67 mmol), 2-chloro-3-pyridine boronic acid pinacol ester (1.34 g, 5.6 mmol), Pd(PPh3)4 (250 mg, 0.22 mmol) and 2M aq.Na2CO3 (7 mL, 14 mmol) in 1,4-dioxane (50 mL). Upon work-up and purification protocol used in the preparation of 6-(2-chloropyridin-3-yl)benzo[d]thiazole provided 5-(2-chloropyridin-3-yl)benzo[d]thiazole as a white solid (820 mg, 70%). 1H NMR (DMSO-d6): δ 9.46 (s, 1H), 8.45 (dd, 1H, J=2.0 and 4.9 Hz), 8.27 (d, 1H, J=8.5 Hz), 8.17 (app s, 1H), 7.97 (dd, 1H, J=1.7 and 7.6 Hz), 7.58 (d, 1H, J=8.5 Hz), 7.53 (dd, 1H, J=4.7 and 7.6 Hz), LCMS: rt 6.73 min (A), purity 99%, MS (m/e) 247.

Aufarbeitung

  1. temperatureby heating
  2. customUpon work-up and purification protocol
  3. customused in the preparation of 6-(2-chloropyridin-3-yl)benzo[d]thiazole

Quellen und Nachweise

ORD-Eintrag
ord-7cc91fbc5aa5487aa27b74c61924af06
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145433B2

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