Sodium Carbonate → HCID 86715478, Verbindung

HRID 2284570

Reaktionsgleichung

Reaktionsgleichung von HRID 2284570
[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.IC1C=C[C:21]2[N:22](C=CN=2)C=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:9]=[CH:10][C:11]3[N:12]([CH:13]=[CH:21][N:22]=3)[CH:16]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 27643276-iodoimidazo[1,2-a]pyridineHCID 120670602-Chloropyridine-3-boronic acid pinacol esterHCID 867154766-(2-Chloropyridin-3-yl)benzo[d]thiazole

Produkt 1

HCID 86715478HCID 86715478, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

6-(2-Chloropyridin-3-yl)imidazo[1,2-a]pyridine was synthesized in the similar to 6-(2-chloropyridin-3-yl)benzo[d]thiazole from 6-iodo-imidazo[1,2-a]pyridine (1.0 g, 4.1 mmol), 2-chloro-3-pyridine boronic acid pinacol ester (1.2 g, 5.0 mmol), Pd(PPh3)4 (250 mg, 0.22 mmol) and 2M aq.Na2CO3 (7 mL, 12 mmol) in 1,4-dioxane (50 mL). Workup of the reaction mixture was carried out by sequential steps of concentrating the reaction mixture, extraction with CH2Cl2, drying over MgSO4/Celite®, filtration and concentration. The crude residue was stirred in 50% EtOAc/hexanes (40 mL). The resulting white precipitate was filtered and dried to provide 6-(2-chloropyridin-3-yl)imidazo[1,2-a]pyridine (0.52 g, 55%). 1H NMR (DMSO-d6): δ 8.73 (dd, 1H, J=0.8 and 1.8 Hz), 8.47 (dd, 1H, J=2.0 and 4.7 Hz), 8.00 (dd, 1H, J=2.0 and 7.6 Hz), 7.98 (s, 1H), 7.64 (d, 1H, J=8.8 Hz), 7.63 (s, 1H), 7.56 (dd, 1H, J=4.7 and 7.6 Hz), 7.33 (dd, 1H, J=1.8 and 8.8 Hz), Hz).LCMS: rt 3.16 min (A), purity 99%, MS (m/e) 230 (MH+).

Aufarbeitung

  1. concentrationof concentrating
  2. extractionthe reaction mixture, extraction with CH2Cl2
  3. dry with materialdrying over MgSO4/Celite®, filtration and concentration
  4. filtrationThe resulting white precipitate was filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8818e424071048ed848a50b056d18235
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145433B2

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