Réaction #1973916

Équation de réaction

9-(2-fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride

9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride

diethylamine

→

9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethyl amide

Rendement 58.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas then added
2. 2
   AutreThe reaction was quenched with 10% aqueous potassium carbonate (2 mL)
3. 3
   AutreThe dichloromethane layer was collected through a phase separator
4. 4
   Concentrationthen concentrated in vacuo
5. 5
   AutreThe crude material was purified by silica gel chromatography
6. 6
   Lavageeluting with petrol (A)
7. 7
   Autreethyl acetate (B) (50-100% (B), 50 g, 35.2 CV, 40 mL/min) to afford a pale yellow solid
8. 8
   AutreThe solid was next triturated with a minimum amount of diethyl ether

Mode opératoire

9-(2-fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride (18) (371 mg, 1.2 mmol) was dissolved in dichloromethane (2 mL) and cooled to 0° C. diethylamine (177 mg, 2.4 mmol, 250 μL) was then added and the reaction was stirred overnight at RT. The reaction was quenched with 10% aqueous potassium carbonate (2 mL). The dichloromethane layer was collected through a phase separator then concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A): ethyl acetate (B) (50-100% (B), 50 g, 35.2 CV, 40 mL/min) to afford a pale yellow solid. The solid was next triturated with a minimum amount of diethyl ether to afford 240 mg (58%) of 9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethyl amide. The structure was confirmed by 13C NMR (75 MHz, CDCl3): δC 13.0, 14.6, 19.9, 21.9, 28.0, 36.3, 40.5, 41.9, 43.1 (d, JCF=23 Hz), 54.7, 82.0 (d, JCF=173 Hz), 99.7, 102.1, 108.3, 117.0, 121.5, 135.3, 137.4, 153.3, and 174.8.

Source