Ammonium Chloride → 7-methyl-1H-pyrazolo[3,4-c]pyridine

HRID 1527295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527295
[CH3:1][Al](C)C.Cl[C:6]1[N:7]=[CH:8][CH:9]=[C:10]2[CH:14]=[N:13][NH:12][C:11]=12.[NH4+].[Cl-]>C1COCC1.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>[CH3:1][C:6]1[N:7]=[CH:8][CH:9]=[C:10]2[CH:14]=[N:13][NH:12][C:11]=12

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 126684917-Chloro-1H-pyrazolo[3,4-c]pyridineHCID 16682925Trimethylaluminum

Produkt 1

HCID 682837107-methyl-1H-pyrazolo[3,4-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Trimethylaluminum (23.9 mL, 47.8 mmol, 2M sol. in toluene) was added to a vigorously stirred solution of 7-chloro-1H-pyrazolo[3,4-c]pyridine (3.67 g, 23.9 mmol) and Pd(PPh3)4 (1.38 g, 1.19 mmol) in THF (109 mL) under argon. The reaction mixture was stirred at 65° C. for 16 h. The mixture was cooled to RT and poured into sat. aq. NH4Cl. The resulting suspension was filtered, the solid washed with water and discarded. The filtrate and the combined washings were extracted with EtOAc (3×). The combined organic extracts were washed with brine then dried (Phase separator) and concentrated under reduced pressure to give 7-methyl-1H-pyrazolo[3,4-c]pyridine as a solid. MS (LC-MS): 134 [M+H]+, tR (HPLC conditions k): 0.25 min.

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe resulting suspension was filtered
  3. washthe solid washed with water
  4. extractionThe filtrate and the combined washings were extracted with EtOAc (3×)
  5. washThe combined organic extracts were washed with brine
  6. customthen dried (Phase separator)
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7c17cfda322e4c70972e06541d8ee815
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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