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

HRID 1878907

반응식

HRID 1878907 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

A mixture of indole-6-boronic acid (0.100 g, 0.615 mol), 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 to 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+].

후처리

  1. stirringto stir 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

출처 및 근거

ORD 기록
ord-3add17858fa34c3bb2c35263d8ed6d53
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314111B2

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