Acetonitrile → HCID 18008503, compound

HRID 2061738Notes

Reaction equation

HRID 2061738 reaction equation
[CH:1](Br)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:21](#[N:23])[CH3:22]>O>[CH:1]([N:23]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:22]=[CH:21]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 236603Bromodiphenylmethane

Product 1

HCID 18008503HCID 18008503, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(Step 4, 1 eq), Ph2CHBr (1.5 eq) and Cs2CO3 (1.5 eq) were mixed in dry acetonitrile (0.1M). The mixture was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with EtOAc. The organic phase was concentrated and the residue was chromatographed with CH2Cl2 as eluent to give the N-benzhydryl indole as an orange gum in 45% yield. m/z (M+H)+ 701.3

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with EtOAc
  4. concentrationThe organic phase was concentrated
  5. customthe residue was chromatographed with CH2Cl2 as eluent

Sources & evidence

ORD record
ord-c6650445aee24f2b807376228544b29c
Source dataset
uspto-grants-2012_10
Patent number
US08283373B2

Reaction notes

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