Phosgene → 1H-indazol-3-yl 4-methylpiperidine-1-carboxylate
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([OH:10])=[N:2]1.[C:11](Cl)(Cl)=[O:12].[CH3:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C1COCC1.C1(C)C=CC=CC=1>[CH3:15][CH:16]1[CH2:21][CH2:20][N:19]([C:11]([O:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:12])[CH2:18][CH2:17]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
300 mg (2.24 mmol) of 1H-indazol-3-ol were dissolved in 25 ml of THF and cooled to −20° C.: 1.3 ml (2.46 mmol) of phosgene in toluene (20 percent) were added dropwise and the reaction mixture was stirred for 90 min, during which it warmed to room temperature. The reaction mixture was concentrated and evacuated once again with a few ml of toluene. The residue was dissolved in 15 ml of THF, 265 μl (2.2 mmol) of 4-methylpiperidine were added dropwise and the mixture was stirred at room temperature for 3 h, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 347 mg (60%), M+H+: 260.4.
Workup
- temperaturewarmed to room temperature
- concentrationThe reaction mixture was concentrated
- stirringthe mixture was stirred at room temperature for 3 h
- concentrationconcentrated
- custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)
Sources & evidence
- ORD record
- ord-161d609aa4d5468cb53f6f06959ad6fe
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528155B2
Reaction notes
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