Hydrochloric Acid → 7-Fluoro-3-[(E)-2-(pyridin-3-yl)-vinyl]-1-trityl-1H-indazole-5-carboxylic Acid
Reaction equation
[F:1][C:2]1[CH:3]=C(C#N)[CH:5]=[C:6]2[C:10]=1[N:9]([C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[N:8]=[C:7]2/[CH:30]=[CH:31]/[C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1.[OH-:40].[K+].Cl.[CH2:43]([OH:45])[CH3:44]>>[F:1][C:2]1[CH:3]=[C:44]([C:43]([OH:40])=[O:45])[CH:5]=[C:6]2[C:10]=1[N:9]([C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[N:8]=[C:7]2/[CH:30]=[CH:31]/[C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1Participants
5
Conditions
- Temperature
- 80 °C
Procedure
3.60 g of 7-fluoro-3-[(E)-2-(pyridin-3-yl)-vinyl]-1-trityl-1H-indazole-5-carbonitrile was dissolved in 500 mL of ethanol, added with 154 g of potassium hydroxide, and stirred at 80° C. overnight. After cooling to room temperature, the solution was adjusted to pH 3 by 5N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and the solvent was evaporated. The obtained crude product was purified by silica gel column chromatography, and the resultant dark brown solid was washed with 10 mL of diethyl ether, to afford 3.58 g of the title compound as dark brown crystals.
Workup
- temperatureAfter cooling to room temperature
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated
- customThe obtained crude product
- customwas purified by silica gel column chromatography
- washthe resultant dark brown solid was washed with 10 mL of diethyl ether
Sources & evidence
- ORD record
- ord-8bfdefd27ac84396be2c72adde113d5d
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429609B2
Reaction notes
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