Nitrogen → 5-[7-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-pyridin-3-ylamine

HRID 341193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341193
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[CH:14]=[CH:15][N:16]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22](Br)[CH:23]=1.C([O-])([O-])=O.[K+].[K+].N#N>CN(C=O)C.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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14]([C:22]4[CH:23]=[C:18]([NH2:17])[CH:19]=[N:20][CH:21]=4)=[CH:15][N:16]=[C:10]3[CH:9]=2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 8176813-Amino-5-bromopyridine2×HCID 593207997-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridine

Produkt 1

HCID 593211075-[7-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-pyridin-3-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To 7-(4-fluoro-phenyl)-imidazo[1,2-a]pyridine (0.1093 g, 0.52 mmol) and 3-amino-5-bromopyridine (0.181 g, 1.05 mmol) in DMF (2 mL) was added 0.5 M K2CO3 (2.06 mL, 1.03 mmol). The reaction vessel was purged with N2 and Pd(PPh3)4 (63 mg, 0.055 mmol) added. The vessel was further purged with N2 and then heated in the microwave at 120° C. for 30 mins. Further 3-amino-5-bromopyridine (0.13 g, 0.75 mmol) and Pd(PPh3)4 (43 mg, 0.037 mmol) were added and the reaction heated in the microwave at 140° C. for 1 hour. The solids were filtered and the filtrate was concentrated in vacuo. The residue was partitioned between H2O (20 ml) and EtOAc (2×20 mL). The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo and the product used crude in the subsequent reaction.

Aufarbeitung

  1. additionadded
  2. customThe vessel was further purged with N2
  3. temperaturethe reaction heated in the microwave at 140° C. for 1 hour
  4. filtrationThe solids were filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was partitioned between H2O (20 ml) and EtOAc (2×20 mL)
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customin the subsequent reaction

Quellen und Nachweise

ORD-Eintrag
ord-d0fec6e4f8084c1d8ebd539e025d9d5e
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895745B2

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