Cesium carbonate → HCID 9823286, compound

HRID 379071Notes

Reaction equation

HRID 379071 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:15]=[C:14]([CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH:13]=[CH:12][C:9]=1[C:10]#[N:11].Br[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]2=[O:37])=[N:28][CH:29]=1>CN(C=O)C>[Cl:36][C:34]1[CH:33]=[CH:32][C:31](=[O:37])[N:30]([C:27]2[CH:26]=[CH:25][C:24]([CH2:23][O:7][C:8]3[CH:15]=[C:14]([CH2:16][N:17]4[CH:21]=[CH:20][N:19]=[CH:18]4)[CH:13]=[CH:12][C:9]=3[C:10]#[N:11])=[CH:29][N:28]=2)[CH:35]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 21696991HCID 21696991, compoundHCID 216970282-Hydroxy-4-imidazol-1-ylmethyl-benzonitrile

Product 1

HCID 9823286HCID 9823286, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (0.123 g, 0.376 mmol) was added to a solution of 2-hydroxy-4-imidazol-1-ylmethyl-benzonitrile (as described in Example 4, Step F) (0.050 g, 0.25 mmol) and 5′-bromomethyl-5-chloro-[1,2′]bipyridinyl-2-one (Step H) (0.079 g, 0.263 mmol) in anhydrous DMF (5 mL) and stirred at ambient temperature overnight. The reaction mixture was partitioned between EtOAc and aqueous saturated NaHCO3 solution, the organic layer separated, washed with H2O, brine and dried (MgSO4). Filtration and concentration to dryness gave the title compound after chromatography (silica gel, 1-4% CH3OH/CH2Cl2). FAB MS 418 (M+1).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and aqueous saturated NaHCO3 solution
  2. customthe organic layer separated
  3. washwashed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-3c7eeeaae4ba4a1e9ca2ae98c658e065
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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