Cesium carbonate → HCID 178504269, compound

HRID 2373347Notes

Reaction equation

HRID 2373347 reaction equation
[CH3:1][Si:2]([CH3:29])([CH3:28])[CH2:3][CH2:4][O:5][CH2:6][NH:7][C:8]([C:10]1[N:14]=[C:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[OH:27])[CH:18]=[CH:19][CH:20]=2)[NH:12][N:11]=1)=[O:9].C(=O)([O-])[O-].[Cs+].[Cs+].[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41]Br)=[CH:39][CH:38]=1>CS(C)=O>[CH3:1][Si:2]([CH3:29])([CH3:28])[CH2:3][CH2:4][O:5][CH2:6][NH:7][C:8]([C:10]1[N:14]=[C:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH2:41][C:40]3[CH:43]=[CH:44][C:37]([F:36])=[CH:38][CH:39]=3)[CH:18]=[CH:19][CH:20]=2)[NH:12][N:11]=1)=[O:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 178504268HCID 178504268, compound

Product 1

HCID 178504269HCID 178504269, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 0.05 g (0.122 mmol) of 2-trimethylsilylethoxymethyl-5-[2′-(hydroxy)biphenyl-3-yl]-1,2,4-triazole-3-carboxamide (prepared according to procedures described in Example 53) in 4 mL of DMSO was added 0.16 g (0.488 mmol) of cesium carbonate and the reaction mixture was stirred at rt for 20 min. To the reaction mixture was added 0.025 mL (0.244 mmol) of 4-fluorobenzylbromide and the reaction mixture was heated at 80° C. for 18 hr. The reaction mixture was partitioned between water and EtOAc. The organic fraction was washed with water and brine, dried (MgSO4) and filtered. The filtrate was concentrated and the residue was purified by chromatography (silica, EtOAc: hexanes, 3:10) to give the title compound.

Workup

  1. temperaturethe reaction mixture was heated at 80° C. for 18 hr
  2. customThe reaction mixture was partitioned between water and EtOAc
  3. washThe organic fraction was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by chromatography (silica, EtOAc: hexanes, 3:10)

Sources & evidence

ORD record
ord-0847a59f617e4a0597538d9cde83aea4
Source dataset
uspto-grants-2008_12
Patent number
US07459475B2

Reaction notes

Loading…