Water → 6-Fluoro-2,3,4,5-tetrahydro-5-(1-methylethyl)-1H-pyrido[4,3-b]indol-1-one
Reaction equation
[F:1][C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:18](Br)([CH3:20])[CH3:19].O>CN(C=O)C>[F:1][C:2]1[C:10]2[N:9]([CH:18]([CH3:20])[CH3:19])[C:8]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of 6-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (1.006 g) in dry DMF (50 ml) was treated with sodium hydride (73.2% dispersion in oil; 333 mg) and stirred under nitrogen for 1 h. Isopropyl bromide (663 mg) was then added, and the solution was stirred at room temperature for 30 min and then at 50° for 12 h. A further portion of isopropyl bromide (150 mg) was then added, and the reaction was then stirred under nitrogen at 50° for ca. 60 h. The mixture was then cooled to room temperature and added to water (300 ml). The mixture was then extracted with dichloromethane (3×200 ml), adsorbed onto silica, and purified by FCC eluting with System A (150:8:1) to give a solid (240 mg) which was triturated with ether to give the title compound (130 mg), m.p. 183°-184°.
Workup
- stirringthe solution was stirred at room temperature for 30 min
- waitat 50° for 12 h
- stirringthe reaction was then stirred under nitrogen at 50° for ca. 60 h
- extractionThe mixture was then extracted with dichloromethane (3×200 ml)
- custompurified by FCC
- washeluting with System A (150:8:1)
Sources & evidence
- ORD record
- ord-911fc99da1d445ce8b41cd05cfa84026
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05183820
Reaction notes
Loading…