Methyl iodide → HCID 59375061, Verbindung

HRID 1811129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811129
[C:1](=O)([O-])[O-].[K+].[K+].IC.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[C:28]2[C:27]3[C:22](=[CH:23][C:24]([OH:29])=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:19]([C:30]([NH2:32])=[O:31])=[CH:18][CH:17]=1>CS(C)=O.CCOC(C)=O>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[C:28]2[C:27]3[C:22](=[CH:23][C:24]([O:29][CH3:1])=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:19]([C:30]([NH2:32])=[O:31])=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59375146HCID 59375146, Verbindung

Produkt 1

HCID 59375061HCID 59375061, VerbindungAusbeute 9,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Potassium carbonate (25.1 mg, 0.182 mmol) and iodomethane (4.9 mL, 0.079 mmol) were added to a solution of 4-(2-fluorophenyl)-7-hydroxy-9H-carbazole-1-carboxamide (Example 40-1, 19.4 mg, 0.061 mmol) in DMSO (1 mL) and the mixture was stirred at rt. After 17 h, the mixture was diluted with EtOAc (30 mL), washed with saturated aqueous ammonium chloride (5 mL), water (2×5 mL), and brine (5 mL), dried and concentrated. The residue was purified by preparative HPLC to provide 4-(2-fluorophenyl)-7-methoxy-9H-carbazole-1-carboxamide (1.9 mg, 9%). 1H NMR (400 MHz, chloroform-d) δ 10.39 (1 H, br. s.), 7.58 (1 H, d, J=7.70 Hz), 7.44-7.55 (2 H, m), 7.28-7.39 (2 H, m), 7.07-7.22 (2 H, m), 7.00 (1 H, d, J=2.20 Hz), 6.65 (1 H, dd, J=8.80, 2.42 Hz), 6.57 (2 H, br. s.), 3.88 (3 H, s). Mass spectrum m/z 335.0 (M+H)+.

Aufarbeitung

  1. washwashed with saturated aqueous ammonium chloride (5 mL), water (2×5 mL), and brine (5 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8f16241c0857419e9b86d019ff1eef0b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362065B2

Notizen zur Reaktion

Wird geladen…