5-Methoxyindole → 5-methoxy-2,3-dihydro-1H-indole

HRID 1014248Notes

Reaction equation

HRID 1014248 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 138725-MethoxyindoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 107019745-methoxy-2,3-dihydro-1H-indoleYield 73.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

At room temperature, to a solution of 5-(methyloxy)-1H-indole (12 g, 81.5 mmol, 1.0 eq) in acetic acid (150 mL) was added sodium cyanoborohydride (10.25 g, 163 mmol, 2.0 eq) in small portions, and the mixture was stirred overnight. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, and dried over Na2SO4. The solvent was removed under reduced pressure to give 5-(methyloxy)-2,3-dihydro-1H-indole (8.91 g, 45% yield) 1H NMR (CDCl3, 300 MHz) δ 6.76 (s, 1H), 6.60 (s, 2H), 3.54 (t, 2H), 3.01 (t, 2H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b6e07a7240ef4988b569e298734fb598
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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