HCID 21696991, compound → HCID 9823286, compound

HRID 1585904Notes

Reaction equation

HRID 1585904 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Br[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]2=[O:31])=[N:22][CH:23]=1>CN(C=O)C>[Cl:30][C:28]1[CH:27]=[CH:26][C:25](=[O:31])[N:24]([C:21]2[CH:20]=[CH:19][C:18]([CH2:17][O:1][C:2]3[CH:9]=[C:8]([CH2:10][N:11]4[CH:15]=[CH:14][N:13]=[CH:12]4)[CH:7]=[CH:6][C:3]=3[C:4]#[N:5])=[CH:23][N:22]=2)[CH:29]=1

Participants

4

Reactant 2

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

Product 1

HCID 9823286HCID 9823286, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy 4-imidazol-1-ylmethyl-benzonitrile (0.050 g, 0.25 mmol) and 5'-bromomethyl-5-chloro-[1,2']bipyridinyl-2-one (Example 10 Step 2) (0.079 g, 0.262 mmol) were dissolved in dry DMF (5 mL), treated with CsCO3 (0.123 g, 0.376 mmol) and stirred at ambient temperature for 18 hr. The reaction mixture was partitioned between EtOAc and aqueous satd NaHCO3 solution, the organic layer washed with H2O, brine, and dried (MgSO4). Chromatography (SiO2, 1-4% CH3OH in CH2Cl2) gave the title compound.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and aqueous satd NaHCO3 solution
  2. washthe organic layer washed with H2O, brine
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-03e0eeb813ac4be2a869433f1a6d05e4
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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