(4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol → 4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 1912552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912552
[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:16]([CH2:17][OH:18])=[C:15]([CH3:19])[N:14]=[C:13]4[N:20]([CH2:23][C:24]5[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=5)[CH:21]=[CH:22][C:12]=34)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:16]([CH:17]=[O:18])=[C:15]([CH3:19])[N:14]=[C:13]4[N:20]([CH2:23][C:24]5[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=5)[CH:21]=[CH:22][C:12]=34)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 71209165(4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanolHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 866757424-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of (4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (967 mg, 2.300 mmol) in dichloromethane (DCM) (24 mL) was treated with PCC (644 mg, 2.99 mmol) and the mixture was stirred at ambient temperature for 90 minutes. The mixture was diluted with dichloromethane, filtered over Celite™ and the filtrate was concentrated. The residue was purified on silica gel (0-70% ethyl acetate/hexanes) to afford the desired product as a pale yellow foam: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.11 (s, 1 H), 7.22 (dd, J=2.1, 8.4 Hz, 1 H), 7.16-7.04 (m, 4 H), 7.04-6.97 (m, 1 H), 6.93 (d, J=8.4 Hz, 1 H), 6.44 (d, J=3.5 Hz, 1 H), 5.47 (s, 2 H), 4.37-4.20 (m, 2 H), 2.95 (s, 3 H), 2.86 (t, J=6.4 Hz, 2 H), 2.20-1.96 (m, 2 H); LC/MS (m/z) ES+=419 (M+1).

Aufarbeitung

  1. filtrationfiltered over Celite™
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified on silica gel (0-70% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-604e89c35b4f49748ebda284243de9c0
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609653B2

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