Water → 4-[3-(1-Benzhydryl-2-methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester

HRID 603970Notes

Reaction equation

HRID 603970 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]=2[CH3:22])=[CH:6][CH:5]=1.[H-].[Na+].[CH:26](Br)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:14]=2[CH3:22])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 236603BromodiphenylmethaneHCID 670554944-[3-(2-Methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester

Product 1

HCID 670555004-[3-(1-Benzhydryl-2-methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of the product from step 2 (1.66 g, 4.86 mmol) in DMF (20 mL) was added NaH (60% in mineral oil, 0.24 g, 5.83 mmol) under N2 atmosphere. The mixture was stirred for 1 h at room temperature, followed by the dropwise addition of benzhydryl bromide (1.8 g, 7.29 mmol) in DMF (5 mL). This reaction mixture was stirred overnight at room temperature. Water (500 mL) was added to reaction mixture, it was extracted with EtOAc, washed with brine, dried (Na2SO4), and concentrated under reduced pressure to a brown syrup, which was purified by silica-gel chromatography using 10% EtOAc/hexanes as eluent to isolate 4-[3-(1-Benzhydryl-2-methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester as a white solid in 76% (1.47 g) yield.

Workup

  1. stirringThis reaction mixture was stirred overnight at room temperature
  2. extractionwas extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure to a brown syrup, which
  6. customwas purified by silica-gel chromatography

Sources & evidence

ORD record
ord-c49dc22e808342f089825e41b9fb4cb8
Source dataset
uspto-grants-2011_03
Patent number
US07906548B2

Reaction notes

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