1-Bromopropane → 5-Chloro-1-propyl-1H-pyrrolo[3,2-b]pyridine

HRID 921022

Reaktionsgleichung

Reaktionsgleichung von HRID 921022
Br[CH2:2][CH2:3][CH3:4].[Cl:5][C:6]1N=[CH:8][C:9]2[NH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[C:15](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:5][C:6]1[N:11]=[C:10]2[CH:12]=[CH:13][N:14]([CH2:2][CH2:3][CH3:4])[C:9]2=[CH:8][CH:15]=1

Komponenten

5

Edukt 3

HCID 78401-BromopropaneHCID 10796Cesium carbonateHCID 457899862-Chloro-5H-pyrrolo[3,2-d]pyrimidine

Produkt 1

HCID 867126215-Chloro-1-propyl-1H-pyrrolo[3,2-b]pyridineAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

1-Bromopropane (192 mg, 1.57 mmol) was added to a solution of 2-chloro-5H-pyrrolo[3,2-d]pyrimidine (200 mg, 1.31 mmol) in DMF (15 mL) followed by cesium carbonate (0.855 g, 2.63 mmol), and the mixture was stirred at 70° C. for 0.5 h. Insoluble solids were filtered off, filtrate was concentrated and partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate and filtered. The filtrate was concentrated in vacuo to afford title compound (0.22 g, 86%) as an oil. 1H NMR (300 MHz, CDCl3): δ 7.59 (d, J=8.7 Hz, 1H), 7.34 (d, J=3.3 Hz, 1H), 7.10 (d, J=8.4 Hz, 1H), 6.62 (d, J=3.6 Hz, 1H), 4.07 (t, J=6.9 Hz, 2H), 1.86 (m, 2H), 0.91 (t, J=7.5 Hz, 3H).

Aufarbeitung

  1. filtrationInsoluble solids were filtered off
  2. concentrationfiltrate was concentrated
  3. custompartitioned between ethyl acetate and water
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-96ffe74c92904414ae1daaeaf32ebb00
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273069B2

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