Phenol → HCID 11709297, compound

HRID 252515Notes

Reaction equation

HRID 252515 reaction equation
[H-].[Na+].Br[CH2:4][C:5]1[N:6]([CH2:18][CH3:19])[C:7]2[C:12]([C:13]=1[C:14]#[N:15])=[CH:11][CH:10]=[C:9]([O:16][CH3:17])[CH:8]=2.[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:18]([N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([O:16][CH3:17])[CH:8]=2)[C:13]([C:14]#[N:15])=[C:5]1[CH2:4][O:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19]

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 59426279HCID 59426279, compound

Product 1

HCID 11709297HCID 11709297, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (44 mg, 4 eq.) in DMF (0.5 mL) is added 2-bromomethyl-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (80 mg, 0.274 mmol) and phenol (2 eq.). After stirring for 20 h, the mixture is poured into ice water and extracted with CH2Cl2. The organic layer is washed with brine and dried with Na2SO4. The solvent is evaporated under vacuum and purified with flash column chromatography on silica gel using EtOAc/petroleum ether (1/5) as eluent to yield 1-ethyl-6-methoxy-2-phenoxymethyl-1H-indole-3-carbonitrile, compound 99.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer is washed with brine
  3. dry with materialdried with Na2SO4
  4. customThe solvent is evaporated under vacuum
  5. custompurified with flash column chromatography on silica gel

Sources & evidence

ORD record
ord-f27ac67e90df43c2ac37ff4e4f8c6690
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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