Methyl iodide → (1-Methyl-1H-indol-6-yl)boronic acid

HRID 1993240Notes

Reaction equation

HRID 1993240 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([B:10]([OH:12])[OH:11])[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:15]1COCC1.CI>>[CH3:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([B:10]([OH:12])[OH:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 27632051H-Indol-6-ylboronic acid

Product 1

HCID 21709054(1-Methyl-1H-indol-6-yl)boronic acid

Procedure

A mixture of indole-6-boronic acid (0.100 g, 0.615 mmol), sodium hydride (0.07 g, 20 mmol) and THF (5 mL, 60 mmol) was stirred at rt for 20 min. then methyl iodide (100 uL, 20 mmol) was added and the mixture was allowed ro stir at rt for 3 hours. The reaction was quenched with sat. NH4Cl solution, washed with brine and dried over Na2SO4, then the solvent was removed in vacuo. The crude product was purified by chromatography over silica gel eluting with 1:9 EtOAc/hexane and 1% MeOH, yielding the desired product. 1H NMR (400 MHz, CDCl3) δ ppm 3.99 (s, 3H), 6.58 (m, 1H). 7.23 (m, 1H), 7.81 (m, 1H), 8.08 (m, 1H) and 8.34 (m, 1H). MS (ES+); m/z 176.15 [MH+].

Workup

  1. stirringstir at rt for 3 hours
  2. customThe reaction was quenched with sat. NH4Cl solution
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThe crude product was purified by chromatography over silica gel eluting with 1:9 EtOAc/hexane and 1% MeOH

Sources & evidence

ORD record
ord-8fa412b1efb7408d944f406759fae38b
Source dataset
uspto-grants-2010_01
Patent number
US07651687B2

Reaction notes

Loading…