2-Morpholinoethanol → 5-(1,3-Dioxolan-2-yl)-3-[2-(morpholin-4-yl)ethoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2I.[N:24]1([CH2:30][CH2:31][OH:32])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2[O:32][CH2:31][CH2:30][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared from 300 mg (0.672 mmol) 5-(1,3-dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole (Example 6A) in analogy to the procedure described in Example 21A. The procedure was modified by using 5 equivalents of 2-(morpholin-4-yl)ethanol as the alcohol reactant and by switching to toluene as solvent. After treating the mixture in a microwave oven at 140° C. for 2 h, the same amounts of catalyst and ligand were added again, and the mixture was refluxed for further 7 days using conventional heating. The crude product was purified by preparative RP-HPLC (acetonitrile/water gradient) to afford 93 mg (30% of th.) of the title compound.
Workup
- additionAfter treating the mixture in a microwave oven at 140° C. for 2 h
- additionthe same amounts of catalyst and ligand were added again
- temperaturethe mixture was refluxed for further 7 days
- customThe crude product was purified by preparative RP-HPLC (acetonitrile/water gradient)
Sources & evidence
- ORD record
- ord-3280c18d738349d4b4b478368aa73419
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08551989B2
Reaction notes
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