Phenol → HCID 11709297, compound

HRID 907122Notes

Reaction equation

HRID 907122 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) was 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 was poured into ice water and extracted with CH2Cl2. The organic layer was washed with brine and dried with Na2SO4. The solvent was 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 was washed with brine
  3. dry with materialdried with Na2SO4
  4. customThe solvent was evaporated under vacuum
  5. custompurified with flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ee3a3e13faa44693aaa5f3093bcce99f
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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