Sodium Hydroxide → HCID 59853489, compound

HRID 2374220Notes

Reaction equation

HRID 2374220 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:27]1[CH:32]=[CH:31][C:30]([CH2:33]Cl)=[CH:29][CH:28]=1.[OH-].[Na+].[I-].[Li+]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][CH2:9][C:10]1[N:11]([CH2:33][C:30]2[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=2)[C:12]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 66321Lithium iodideHCID 745714-(Chloromethyl)pyridineHCID 178491710HCID 178491710, compound

Product 1

HCID 59853489HCID 59853489, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sulfide 36 (247 mg, 0.67 mmol) in THF (10 mL) was added 4-picolylchloride (220 mg, 1.34 mmol), powder NaOH (59 mg, 1.47 mmol), lithium iodide (44 mg, 0.33 mmol), and tetrabutylammonium bromide (22 mg, 0.067 mmol). See Scheme 22. After the reaction mixture was stirred for 2 d at room temperature, the mixture was partitioned between EtOAc and sat. NH4Cl. The organic phase was dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude product was chromatographed on silica gel (eluting 60-100% EtOAc/hexane) to give 4-[2-benzyloxymethyl-4-isopropyl-5-(3-methoxy-phenylsulfanyl)-imidazol-1-ylmethyl]-pyridine 37 (201 mg, 65%) as a yellow oil.

Workup

  1. customthe mixture was partitioned between EtOAc and sat. NH4Cl
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude product was chromatographed on silica gel (eluting 60-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-f39de0e5bb834b81861665f177862042
Source dataset
uspto-grants-2008_12
Patent number
US07462608B2

Reaction notes

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