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Sodium Carbonate → 1-methyl-3-(1-methylindolin-6-yl)-4-nitro-1H-pyrrolo[2,3-b]pyridine

HRID 331004
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 331004
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH3:14])[CH:3]=1.[CH3:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22](B3OC(C)(C)C(C)(C)O3)[CH:23]=2)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(Cl)Cl.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:14][N:4]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[C:10]2[C:2]([C:22]2[CH:23]=[C:24]3[C:19]([CH2:18][CH2:17][N:16]3[CH3:15])=[CH:20][CH:21]=2)=[CH:3]1
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Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 709799671-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolineHCID 710900843-Iodo-1-methyl-4-nitro-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 710903071-methyl-3-(1-methylindolin-6-yl)-4-nitro-1H-pyrrolo[2,3-b]pyridineAusbeute 49,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 6342AcetonitrileLösungsmittel
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a stirred solution of 3-iodo-1-methyl-4-nitro-1H-pyrrolo[2,3-b]pyridine (D17) (6.2 g, 20.46 mmol) in ACN (108 mL) was added 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline (7.95 g, 30.7 mmol), bis(triphenylphosphine)palladium(II) chloride (1.436 g, 2.046 mmol) and 2M sodium carbonate aq. solution (108 mL, 217 mmol). The resulting mixture was heated at 65° C. for ca. 1 hour. After being cooled to RT, the reaction mixture was diluted with DCM (150 mL) and water (200 mL). The organic phase was separated and the aqueous phase was further extracted with DCM (80 mL×4). The combined organics were dried and concentrated. The residue was purified by chromatography on silica, eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give an impure fraction which was re-purified by chromatography on silica, eluting with a gradient of 0-20% ethyl acetate in DCM to give the title compound (3.14 g). LCMS (A): m/z (M+H)+ 309, C17H16N4O2 requires 308 (acidic).

Aufarbeitung

  1. temperatureAfter being cooled to RT
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was further extracted with DCM (80 mL×4)
  4. customThe combined organics were dried
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica
  7. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane
  8. customto give an impure fraction which
  9. customwas re-purified by chromatography on silica
  10. washeluting with a gradient of 0-20% ethyl acetate in DCM

Quellen und Nachweise

ORD-Eintrag
ord-a1511065559c4e89aa17e233d2af7315
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877742B2

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