Trimethyl borate → (1-Methyl-1H-indol-2-yl)boronic acid
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.C([Li])(CC)C.[B:16](OC)([O:19]C)[O:17]C>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[B:16]([OH:19])[OH:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
1-Methylindole (0.38 mL, 3 mmol) was dissolved in THF (10 mL), and the solution was cooled to −78° C. To this solution was added sec-butyllithium (1.9 mL, 2.5 mmol), and the reaction mixture was stirred for 20 minutes. Trimethyl borate (0.34 mL, 3 mmol) was added at −78° C., and the mixture was stirred and allowed to warm to room temperature. The reaction was quenched with water, and the solvents were removed under vacuum. The residue was taken directly to the next step.
Workup
- stirringthe mixture was stirred
- temperatureto warm to room temperature
- customThe reaction was quenched with water
- customthe solvents were removed under vacuum
Sources & evidence
- ORD record
- ord-a2df0d4af4ad419e8774aeae7caeb460
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06437138B1
Reaction notes
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