Water → 5-(Cyclopentylmethyl)-6-fluoro-2,3,4,5-tetrahydro-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+].CS([O-])(=O)=O.O.C(O[CH2:28][CH3:29])(=O)C>CN(C=O)C>[CH:28]1([CH2:29][N:9]2[C:10]3[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=3[C:7]3[C:14](=[O:15])[NH:13][CH2:12][CH2:11][C:8]2=3)[CH2:4][CH2:3][CH2:2][CH2:10]1Participants
Reactant 5
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 (1.023 g) in dry DMF (50 ml) was treated with sodium hydride (73.2% dispersion in oil; 331 mg) and stirred under nitrogen at room temperature for 30 min. A solution of cyclopentylmethyl(methyl sulphonate (893 mg) in dry DMF (20 ml) was then added over 15 min and stirring was continued for 5 days. Water (20 ml) was added to the reaction mixture which was then concentrated in vacuo to give a solid. This was dissolved in ethyl acetate (300 ml) and methanol (1 ml), and the resulting solution was washed with saturated sodium chloride solution (3×100 ml) and then adsorbed onto silica. Purification by FCC eluting with System A (150:8:1) gave a solid (283 mg) which was recrystallised from ethyl acetate to give the title compound (237 mg) m.p. 175°-176°.
Workup
- stirringstirring
- waitwas continued for 5 days
- concentrationwas then concentrated in vacuo
- customto give a solid
- washmethanol (1 ml), and the resulting solution was washed with saturated sodium chloride solution (3×100 ml)
- customPurification by FCC
- washeluting with System A (150:8:1)
Sources & evidence
- ORD record
- ord-0d1ef148327d4424bca89da57bed37de
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05183820
Reaction notes
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