Cesium carbonate → HCID 18008503, compound

HRID 225992Notes

Reaction equation

HRID 225992 reaction equation
[Si](OCC[C:21]1[NH:22][C:23]2[C:28]([C:29]=1C(=O)C(OCC)=O)=[CH:27][C:26](Cl)=[CH:25][CH:24]=2)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:38](Br)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C.O>[CH:38]([N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:21]1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 236603BromodiphenylmethaneHCID 67055447HCID 67055447, compound

Product 1

HCID 18008503HCID 18008503, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Ethyl [2-({[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-chloro-1H-indol-3-yl](oxo)acetate (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-f571e3116838431584c1778f94e0dd23
Source dataset
uspto-grants-2009_07
Patent number
US07557135B2

Reaction notes

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