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Trimethyl borate → (1-Methyl-1H-indol-2-yl)boronic acid

HRID 365821
Notes
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Reaction equation

HRID 365821 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 117811-MethylindoleHCID 178418400CID 53628100

Product 1

HCID 22733820(1-Methyl-1H-indol-2-yl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 mnL, 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

  1. stirringthe mixture was stirred
  2. temperatureto warm to room temperature
  3. customThe reaction was quenched with water
  4. customthe solvents were removed under vacuum

Sources & evidence

ORD record
ord-e0897dc319364c3086dff7a8a8ea75f2
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06127386

Reaction notes

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