Water → 6-Fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(4-methyloxazol-5-yl)methyl]-1H-pyrido[4,3-b]indol-1-one
Reaction equation
[H-].[Na+].[F:3][C:4]1[C:12]2[N:11]([CH3:13])[C:10]3[CH2:14][CH2:15][NH:16][C:17](=[O:18])[C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1.Cl[CH2:20][C:21]1[O:25][CH:24]=[N:23][C:22]=1[CH3:26].O>COCCOC>[F:3][C:4]1[C:12]2[N:11]([CH3:13])[C:10]3[CH2:14][CH2:15][N:16]([CH2:20][C:21]4[O:25][CH:24]=[N:23][C:22]=4[CH3:26])[C:17](=[O:18])[C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium hydride (73% dispersion in oil; 167 mg) was added to a stirred suspension of 6-fluoro-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (500 mg) in dry DME (150 ml), and the suspension was stirred at 60° under nitrogen for 6 h. 5-Chloromethyl-4-methyloxazole (440 mg) was then added and the mixture was stirred overnight at 60°. A further quantity of sodium hydride (73% dispersion in oil; 84 mg) was added and the mixture was stirred for 3 h, and then cooled (0°). Water (200 ml) was added, and the mixture was extracted with dichloromethane (3×200 ml). The combined organic extracts were concentrated in vacuo and the residue was purified by FCC eluting with System A (100:8:1) to give the title compound (550 mg) as a solid, m.p. 158°-161°.
Workup
- stirringthe mixture was stirred overnight at 60°
- stirringthe mixture was stirred for 3 h
- temperaturecooled (0°)
- extractionthe mixture was extracted with dichloromethane (3×200 ml)
- concentrationThe combined organic extracts were concentrated in vacuo
- customthe residue was purified by FCC
- washeluting with System A (100:8:1)
Sources & evidence
- ORD record
- ord-93ffe51ec0074f0cad1bf2034c275454
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05183820
Reaction notes
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