Sodium Hydroxide → 6-hydroxy-1-ethyl-1H-indole-3-carbonitrile

HRID 502107Notes

Reaction equation

HRID 502107 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[C:5]([C:14]#[N:15])=[CH:4]1)[CH3:2].B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[OH:12][C:9]1[CH:10]=[C:11]2[C:6]([C:5]([C:14]#[N:15])=[CH:4][N:3]2[CH2:1][CH3:2])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 116441001-ethyl-6-methoxy-1H-indole-3-carbonitrile

Product 1

HCID 594250606-hydroxy-1-ethyl-1H-indole-3-carbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-ethyl-6-methoxy-1H-indole-3-carbonitrile (2.85 g, 14.2 mmol), prepared by example 1A, step B, in CH2Cl2 (40 mL) is added a 1M solution of BBr3 in CH2Cl2 (28.5 mL, 28.5 mmol) at 0° C. The mixture is allowed to warm to room temperature and kept for 2.5 h. The dark reaction mixture is then poured onto ice and sufficient 1M NaOH is added until the pH is 8-9. The product is extracted with CH2Cl2 (3×) and the combined organic phases are washed with saturated NaHCO3, H2O and saturated NaCl. After drying over MgSO4, the solution is concentrated and the product is purified by chromatography (EtOAc/CH2Cl2, 0-10%) to afford 2.15 g (82%) of 6-hydroxy-1-ethyl-1H-indole-3-carbonitrile as a yellow solid.

Workup

  1. customThe dark reaction mixture
  2. additionis added until the pH is 8-9
  3. extractionThe product is extracted with CH2Cl2 (3×)
  4. washthe combined organic phases are washed with saturated NaHCO3, H2O and saturated NaCl
  5. dry with materialAfter drying over MgSO4
  6. concentrationthe solution is concentrated
  7. customthe product is purified by chromatography (EtOAc/CH2Cl2, 0-10%)

Sources & evidence

ORD record
ord-f80b624d4dab4b3380909a72edfd07c3
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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