Cesium carbonate → 1-cyclopentyl-5-iodo-1H-indazole
Reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=O.[CH:11]1([NH:16][NH2:17])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC([O-])(C)C.[K+]>CN1C(=O)CCC1.C(OCC)(=O)C.C(#N)C.CN(C=O)C>[CH:11]1([N:16]2[C:2]3[C:3](=[CH:6][C:7]([I:10])=[CH:8][CH:9]=3)[CH:4]=[N:17]2)[CH2:15][CH2:14][CH2:13][CH2:12]1Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2-fluoro-5-iodobenzaldehyde (500 mg, 2 mmol), cyclopentylhydrazine (273 mg, 2 mmol), and cesium carbonate (1.91 g, 5 mmol) in NMP (5 ml) was stirred at 100° C. overnight. Then KOtBu (560 mg, 5 mmol) and DMF (10 ml) were added, and the mixture was stirred at 150° C. for 5 h. After cooling to r.t., the mixture was diluted with ethyl acetate (100 ml), and washed with water (3×50 ml), and dried. Evaporation of solvent afforded batch residue, which was dissolved in acetonitrile (50 ml), and the insoluble material was removed by filtration. Flash chromatography on silica gel (n-heptane/ethyl acetate) afforded yellow oil, 158 mg (25%).
Workup
- stirringthe mixture was stirred at 150° C. for 5 h
- temperatureAfter cooling to r.t.
- washwashed with water (3×50 ml)
- customdried
- customEvaporation of solvent
- customafforded batch residue, which
- customthe insoluble material was removed by filtration
- customFlash chromatography on silica gel (n-heptane/ethyl acetate) afforded yellow oil, 158 mg (25%)
Sources & evidence
- ORD record
- ord-8fe542c983ec478994c8c0d5ada4321b
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728030B2
Reaction notes
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