Hexane → HCID 10758603, compound

HRID 650574

Reaction equation

HRID 650574 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:12])[NH:7]2.[H-].[Na+].CCCCCC.Cl[CH2:22][C:23]1[CH:24]=[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:27][CH:28]=1>CN(C=O)C.O>[C:25]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=3)[CH:5]=[C:6]2[CH3:12])[CH:24]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 107732744-methoxy-2-methyl-1H-indoleHCID 154808923-(Chloromethyl)-1,1'-biphenyl

Product 1

HCID 10758603HCID 10758603, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

805 mg (5 mmol) of 4-methoxy-2-methyl-1H-indole is reacted with 200 mg (5 mmol) of 60% NaH/mineral oil (washing with hexane before adding DMF) in 15 mL of DMF and after stirring for 0.5 hour, 1.0 g (5 mmol) of 3-(chloromethyl)biphenyl is added. The mixture is stirred at room temperature for 18 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate solution is washed with brine, dried (MgSO4) and after concentrating at reduced pressure, the residue is chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.25 g (76% yield) of 1-((1,1′-biphenyl)-3-ylmethyl)-2-methyl-4-methoxy-1H-indole mp, 127°-131° C.

Workup

  1. stirringThe mixture is stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate solution is washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationafter concentrating at reduced pressure
  6. customthe residue is chromatographed on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-bdc8da2278f6451085810f4fd9bb8c02
Source dataset
uspto-grants-2001_08
Patent number
US06274616B1

Linked notes

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