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

HRID 624038

Reaction equation

HRID 624038 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-indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-methoxyindole (500 mg, 3.39 mmol) in acetic acid (34 mL), sodium cyanoborohydride (641 mg, 10.20 mmol) was added in portions. After stirring for 30 min at rt, the mixture was quenched with water (2.0 mL) and concentrated. The yellow residue was dissolved in DCM, washed with aq. sat. NaHCO3-solution and brine. The org. layers was dried (MgSO4), filtered and the solvent removed under reduced pressure to yield 5-methoxyindoline which was stored in the freezer. LC-MS conditions B: tR=0.24 min, [M+H]+=150.09.

Workup

  1. customthe mixture was quenched with water (2.0 mL)
  2. concentrationconcentrated
  3. dissolutionThe yellow residue was dissolved in DCM
  4. washwashed with aq. sat. NaHCO3-solution and brine
  5. dry with materiallayers was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-79a21aeeab26494e803fecfef70fd1ca
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Linked notes

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