Furan-3-boronic acid → 4-(3-Chloro-phenylethynyl)-1-furan-3-yl-2-methyl-1H-imidazole

HRID 1294491

Reaction equation

HRID 1294491 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[NH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[O:16]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17]1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[N:13]([C:18]3[CH:19]=[CH:20][O:16][CH:17]=3)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 178432693HCID 178432693, compound

Product 1

HCID 668795994-(3-Chloro-phenylethynyl)-1-furan-3-yl-2-methyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Chloro-phenylethynyl)-2-methyl-1H-imidazole (200 mg, 0.92 mmol) was dissolved in 10 mL dichloromethane. Powdered molecular sieves (3 A, 200 mg), 3-furaneboronic acid (207 mg, 1.85 mmol) and [Cu(OH)TMEDA]2Cl2 (43 mg, 0.093 mmol) were added. Oxygen was bubbled through the reaction mixture for 10 minutes and stirring was continued at room temperature overnight. The reaction mixture was filtered through a dicalite speed plus pad and washed with 50 mL dichloromethane. The filtrate was washed with 50 mL water, dried with magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient) and the desired compound was as a brown oil (21 mg, 8%), MS: m/e=283.1 (M+H+).

Workup

  1. customOxygen was bubbled through the reaction mixture for 10 minutes
  2. filtrationThe reaction mixture was filtered through a dicalite speed plus pad
  3. washwashed with 50 mL dichloromethane
  4. washThe filtrate was washed with 50 mL water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient)

Sources & evidence

ORD record
ord-90ea6191f94d4d1b9dd601134cd6cfc3
Source dataset
uspto-grants-2007_07
Patent number
US07241760B2

Linked notes

Loading…