Pyridine → HCID 66697274, compound

HRID 2096803Notes

Reaction equation

HRID 2096803 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].N1C=CC=CC=1.[Cl:21][C:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:23]=1[CH:29]([CH3:48])[C:30]([C:36]1[CH:47]=[CH:46][C:39]2[N:40]([CH3:45])[C:41](=[O:44])[N:42]([CH3:43])[C:38]=2[CH:37]=1)([OH:35])[C:31]([F:34])([F:33])[F:32]>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:11][O:10][C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([O:28][C:26]2[CH:25]=[CH:24][C:23]([CH:29]([CH3:48])[C:30]([C:36]3[CH:47]=[CH:46][C:39]4[N:40]([CH3:45])[C:41](=[O:44])[N:42]([CH3:43])[C:38]=4[CH:37]=3)([OH:35])[C:31]([F:32])([F:33])[F:34])=[C:22]([Cl:21])[CH:27]=2)=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27828183-Fluoro-4-(methoxycarbonyl)benzeneboronic acidHCID 59507321HCID 59507321, compound

Product 1

HCID 66697274HCID 66697274, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Copper(II)acetate (657 mg), 3-fluoro-4-methoxycarbonylphenylboronic acid (CAS Reg. 505083-04-5, 716 mg), and pyridine (0.3 ml) were added to a solution of 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (Example 85, 500 mg) in DCM (20 ml). The mixture was stirred with molecular sieves under air atmosphere for 4 days and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, 2:1 EtOAc/heptane) to give the title compound (400 mg) as a light yellow oil. MS (m/e)=567.1 [M+H+].

Workup

  1. concentrationconcentrated to an oil
  2. customThe residue was purified by flash chromatography (SiO2, 2:1 EtOAc/heptane)

Sources & evidence

ORD record
ord-98f5708a08d64a8eb1e686feb8f39608
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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