Sodium hydride → methyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

HRID 992560

Reaktionsgleichung

Reaktionsgleichung von HRID 992560
[H-].[Na+].[CH:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[C:5]([C:16]([O:18][CH3:19])=[O:17])[N:4]=1.[Na].C1C2NC3C(=CC=CC=3)C=2C=CN=1.[Cl:34][C:35]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:36]=1[CH2:37]Cl>CN(C=O)C.O>[Cl:34][C:35]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:36]=1[CH2:37][N:14]1[C:15]2[CH:3]=[N:4][C:5]([C:16]([O:18][CH3:19])=[O:17])=[CH:6][C:7]=2[C:8]2[C:13]1=[CH:12][CH:11]=[CH:10][CH:9]=2

Komponenten

8

Edukt 5

HCID 24758Sodium hydrideHCID 64961Beta-CarbolineHCID 759762,5-Dichlorobenzyl chlorideHCID 107704Methyl 9H-pyrido(3,4-b)indole-3-carboxylateHCID 5360545Sodium

Produkt 1

HCID 9908122methyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (1.60 g of 60% dispersion in oil, 0.04 mol) in dry DMF (60 mL) was added methyl 9H-β-carboline-3-carboxylate (8.7 g, 0.0385 mol) at −20° C. with stirring. The mixture was allowed to warm to room temperature with stirring under nitrogen. After stirring for 10 minutes at room temperature, formation of the sodium salt of the β-carboline appeared to be complete, resulting in a clear brown solution. The reaction mixture was cooled in an ice bath, 2,5-dichlorobenzyl chloride (7.82 g, 0.040 mol) was added, and the mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with water (200 mL), filtered, and the cake washed with water, ethyl acetate, ether, and dried, affording 13.05 g (88%) of the title product. 1H NMR (CDCl3) δ8.88 (s, 1H), 8.78 (s, 1H), 8.20 (d, J=7.8 Hz, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.45-7.35 (m, 3H) 7.18 (dd, J=8.2, 1.7 Hz,1H), 6.52 (s, 1H), 5.56 (s, 2H), 4.06 (s, 3H); MS (APCI; (M+H)+) m/z 385.

Aufarbeitung

  1. stirringwith stirring under nitrogen
  2. stirringAfter stirring for 10 minutes at room temperature
  3. customresulting in a clear brown solution
  4. temperatureThe reaction mixture was cooled in an ice bath
  5. temperatureto warm to room temperature
  6. stirringstirred overnight
  7. filtrationfiltered
  8. washthe cake washed with water, ethyl acetate, ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d9f8c7acaab742b78147fe775900c25b
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06469021B1

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