Reaction equation
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([B:17]3[O:25]C(C)(C)C(C)(C)[O:18]3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CC(C)=O.O>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([B:17]([OH:25])[OH:18])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To N-Boc-indazole-5-boronic acid pinacol ester (S46) (390 mg, 1.13 mmol, 1.00 equiv) in acetone/H2O (5.0 mL/5.0 mL) at 23° C. was added NH4OAc (436 mg, 5.65 mmol, 5.00 equiv) and NaIO4 (1.21 g, 5.65 mmol, 5.00 equiv). After stiffing for 48 hr at 23° C., the reaction mixture was concentrated in vacuo to remove acetone. To the residual solution was added EtOAc (5 mL) and the phases were separated. The aqueous phase was extracted with EtOAc (2×5 mL). The combined organic phases are washed with brine (10 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was triturated with Et2O to afford 200 mg of the title compound as a colorless solid (68% yield).
Workup
- concentrationthe reaction mixture was concentrated in vacuo
- customto remove acetone
- additionTo the residual solution was added EtOAc (5 mL)
- customthe phases were separated
- extractionThe aqueous phase was extracted with EtOAc (2×5 mL)
- washThe combined organic phases are washed with brine (10 mL)
- dry with materialdried (Na2SO4)
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was triturated with Et2O
Sources & evidence
- ORD record
- ord-90458706fc9e4692b04136d2a565b03b
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09024093B2
Linked notes
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