Pyridine → HCID 66616168, compound

HRID 2172146Notes

Reaction equation

HRID 2172146 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][NH:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:15]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)([O:17][CH3:18])=[O:16].N1C=CC=CC=1>ClCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[CH:12][N:13]([C:23]3[CH:24]=[C:19]([CH:20]=[CH:21][CH:22]=3)[C:15]([O:17][CH3:18])=[O:16])[CH:14]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 178438898HCID 178438898, compound

Product 1

HCID 66616168HCID 66616168, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-isopropyl-phenyl)-1H-imidazole (190 mg), 3-carbomethoxy-phenylboronic acid (360 mg) and Cu(OAc)2 (300 mg) in dichloromethane (15 mL) is treated with pyridine (160 mg) and 4 Å molecular sieves (500 mg). The mixture is stirred in the presence of air for 14 h then filtered through celite, and the celite pad is washed well with ethyl acetate. The filtrate and washing are combined and evaporated, and the residual material is separated by column chromatography to afford the product, methyl 3-[4-(4-isopropyl-phenyl)-imidazol-1-yl]-benzoate, as a yellow solid (190 mg).

Workup

  1. filtrationthen filtered through celite
  2. washthe celite pad is washed well with ethyl acetate
  3. washThe filtrate and washing
  4. customevaporated
  5. customthe residual material is separated by column chromatography

Sources & evidence

ORD record
ord-e2dbc06e18fd4603804335a2536f1b42
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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