Water → HCID 18008503, compound

HRID 225985Notes

Reaction equation

HRID 225985 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6](CCNS(CC1C(Br)=CC=CC=1Br)(=O)=O)=[C:5]2CCCC1C=CC(C(O)=O)=CC=1.[H-].[Na+].C(Br)(C1C=CC=CC=1)C1C=CC=CC=1.O>CN(C=O)C>[CH:11]([N:7]1[C:8]2[C:4](=[CH:3][CH:2]=[CH:10][CH:9]=2)[CH:5]=[CH:6]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 236603BromodiphenylmethaneHCID 15950319HCID 15950319, compound

Product 1

HCID 18008503HCID 18008503, compoundYield 106.7%

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, and the mixture 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 the N-benzhydrylindole as a white solid (1.47 g) in 59% yield.

Workup

  1. stirringThis reaction mixture was stirred overnight at room temperature
  2. extractionthe mixture was 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-b40b6b09314f44659d23565057ef1ae0
Source dataset
uspto-grants-2009_07
Patent number
US07557135B2

Reaction notes

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