Potassium Iodide → ethyl [(3'-{[3-(diphenylmethyl)-6-oxopyridazin-1(6H)-yl]methyl}biphenyl-3-yl)oxy]acetate

HRID 2389311Notes

Reaction equation

HRID 2389311 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Li+].CS(O[CH2:28][C:29]1[CH:30]=[C:31]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:36]=2)[CH:32]=[CH:33][CH:34]=1)(=O)=O.[I-].[K+]>CN(C=O)C>[C:15]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:14])[N:12]([CH2:28][C:29]3[CH:30]=[C:31]([C:35]4[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:36]=4)[CH:32]=[CH:33][CH:34]=3)[N:13]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 62714Lithium hydrideHCID 543237696-diphenylmethyl-3(2H)-pyridazinoneHCID 86637887Ethyl [(3'-{[(methylsulfonyl) oxy]methyl}biphenyl-3-yl)oxy]acetate

Product 1

HCID 86637886ethyl [(3'-{[3-(diphenylmethyl)-6-oxopyridazin-1(6H)-yl]methyl}biphenyl-3-yl)oxy]acetateYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-(diphenylmethyl)pyridazin-3(2H)-one (97.2 mg) in DMF (2.7 mL) was added LiH (5.89 mg) at ambient temperature. After 5-minutes, ethyl [(3′-{[(methylsulfonyl) oxy]methyl}biphenyl-3-yl)oxy]acetate (135 mg) in DMF (1 mL) and potassium iodide (12.3 mg) were added to the solution at ambient temperature and stirred for 5 hours. The resulting mixture was quenched with 1M HCl aqueous solution and diluted with EtOAc. The organic layer was washed successively with water and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=100:0-97:3) to give ethyl [(3′-{[3-(diphenylmethyl)-6-oxopyridazin-1(6H)-yl]methyl}biphenyl-3-yl)oxy]acetate (187 mg) as a colorless gum.

Workup

  1. waitAfter 5-minutes
  2. customThe resulting mixture was quenched with 1M HCl aqueous solution
  3. additiondiluted with EtOAc
  4. washThe organic layer was washed successively with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=100:0-97:3)

Sources & evidence

ORD record
ord-c71ad1d23e234c0cbc59fc20dc9655c0
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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