1h-Pyrrolo[2,3-c]pyridine-2-methanol,a-(4-methylphenyl)- → (4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

HRID 1821885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821885
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[NH:18][C:13]3=[CH:14][N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)[OH:9])=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[NH:18][C:13]3=[CH:14][N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)=[O:9])=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 578934571h-Pyrrolo[2,3-c]pyridine-2-methanol,a-(4-methylphenyl)-

Produkt 1

HCID 57893512(4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanoneAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(4-Methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (Example 98) (225 mg, 0.94 mmol) was dissolved in methylene chloride (15 mL). Manganese dioxide (817 mg, 9.40 mmol) was added and the reaction mixture was stirred for ca. 14 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed several times with hot ethanol. The filtrate was concentrated to give a white solid. Drying under vacuum produced (4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (149 mg, 67%) as a white solid: mp 264-268° C. dec.; 1H NMR (300 MHz, CD3OD) δ2.47 (3H, s), 7.18 (1H, s), 7.41 (2H, d, J=7.9 Hz), 7.73-7.75 (1H, m), 7.92 (2H, d, J=8.1 Hz), 8.16 (1H, d, J=5.6 Hz), 8.87 (1H, s); ESI MS m/z 237 [C15H12N2O+H]+; HPLC (Method A) 93.4% (AUC), tR=15.9 min.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed several times with hot ethanol
  3. concentrationThe filtrate was concentrated
  4. customto give a white solid
  5. customDrying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b4a0acdea8374ba086525c42a273fefb
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608627B2

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