Ethyl 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylate → 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylic acid
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([O:18]CC)=[O:17])[CH:14]=3)[N:9]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]=2)=[CH:3][CH:2]=1>C1COCC1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=3)[N:9]([C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]=2)=[CH:3][CH:2]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a 5 ml microwave vial equipped with a stir bar was added ethyl 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylate (816 mg, 1.601 mmol), LOH (2402 μl, 2.402 mmol), and THF (8006 μl). The vial was sealed and heated to 50° C. for 19 hours, after which the LCMS indicates formation of the desired product. Crude was quenched with HCl (2402 μl, 2.402 mmol) and the reaction was concentrated in vacuo. Material was dry loaded onto a 100 g column; was run from 100% dichloromethane to 25% methanol. Desired product eluted; fractions were collected and concentrated in vacuo to a white solid.