Cesium carbonate → Methyl [1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl](oxo)acetate

HRID 2301669Notes

Reaction equation

HRID 2301669 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[NH:11][C:12]2[C:17]([C:18]=1[C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:16][C:15]([Cl:25])=[CH:14][CH:13]=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[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.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH:26]([N:11]1[C:12]2[C:17](=[CH:16][C:15]([Cl:25])=[CH:14][CH:13]=2)[C:18]([C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21])=[C:10]1[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 236603BromodiphenylmethaneHCID 90772388Methyl [2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1h-indol-3-yl](oxo)acetate

Product 1

HCID 86758767Methyl [1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl](oxo)acetateYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl [2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl](oxo)acetate (1 eq), Ph2CHBr (2 eq) and Cs2CO3 (1.5 eq) were mixed in dry acetonitrile (0.13M) under N2. The mixture was heated with stirring to reflux for 3 hrs. The reaction mixture was cooled to rt and filtered and solvent was removed. Resulting residue was purified using a column with 1:4Hexane/CH2Cl2 as eluent to give methyl [1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy }methyl)-5-chloro-1H-indol-3-yl](oxo)acetate (yellow-brown solid) in 60% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hrs
  3. filtrationfiltered
  4. customsolvent was removed
  5. customResulting residue was purified

Sources & evidence

ORD record
ord-5d35a49db6e440a3a8f38399b8580ae9
Source dataset
uspto-grants-2002_12
Patent number
US06500853B1

Reaction notes

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