Dimethylformamide → 5-bromo-1-(4-hydroxyphenyl)-2-methyl-1H-indole-3-carbaldehyde

HRID 1297272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1297272
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]1[CH:21]=[CH:20][C:19]([O:22]COC)=[CH:18][CH:17]=1)[C:11]([CH3:26])=[CH:10]2.CN(C)[CH:29]=[O:30]>>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:11]([CH3:26])=[C:10]2[CH:29]=[O:30]

Komponenten

4

Edukt 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 693000525-Bromo-1-(4-methoxymethyloxyphenyl)-2-methyl-1H-indole

Produkt 1

HCID 860346135-bromo-1-(4-hydroxyphenyl)-2-methyl-1H-indole-3-carbaldehydeAusbeute 51 %

Versuchsvorschrift

Phosphorous oxychloride (2.5 mL) was added to anhydrous dimethylformamide (5 mL) and stirred at room temperature for 15 min whereupon a solution of 5-bromo-1-(4-methoxymethyloxyphenyl)-2-methyl-1H -indole (0.65 g, 1.9 mmol) in dimethylformamide (10 mL) was added. The solution was reacted according to the procedure used in Example 2a to afford a tan solid (51%): mp>250° C.; 1H NMR (DMSO-d6): δ 2.50 (3H, s), 6.95-7.02 (3 H, m), 7.21 (1H, dd, J=2.4 Hz, J=8.8 Hz), 7.28 (2H, d, J=8.7 Hz), 8.38 (1H, d, J=2.2 Hz), 9.98 (1H, s), 10.14 (1H, s); MS m/Z (M+H)+ 318/320 (1 Br). Anal. for C16H12BrNO2·0.2H2O: Calc'd: C, 55.99; H, 3.88; N, 4.35. Found: C, 55.69; H, 3.95; N, 4.15.

Aufarbeitung

  1. additionwas added
  2. customThe solution was reacted

Quellen und Nachweise

ORD-Eintrag
ord-d2f6cfaeb58d46c285c8cd9597387212
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250440B2

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