Methanol → ethyl 6-[p-[5-(1H-imidazo[4,5-b]pyridin-2-ylthio)pentyloxy]phenoxy]-2,2-dimethylhexanoate

HRID 329463

Reaction equation

HRID 329463 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.CO.[OH-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:40]=[CH:39][C:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([CH3:38])([CH3:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:24][CH:23]=1>O>[NH:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:10]=[C:2]1[S:1][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:40]=[CH:39][C:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([CH3:38])([CH3:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 14851566Ethyl 6-[p-(5-bromopentyloxy)phenoxy]-2,2-dimethylhexanoateHCID 178527819HCID 178527819, compound

Product 1

HCID 14327306ethyl 6-[p-[5-(1H-imidazo[4,5-b]pyridin-2-ylthio)pentyloxy]phenoxy]-2,2-dimethylhexanoateYield 32.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 570 mg 2-mercapto-1H-imidazo[4,5-b]pyridine and 18 ml methanol, was added a mixture of 166 mg sodium hydroxide, 6 ml water and 1.8 g ethyl 6-[p-(5-bromopentyloxy)phenoxy]-2,2-dimethylhexanoate. The resulting mixture was heated under reflux for 12 hours, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography, affording 610 mg ethyl 6-[p-[5-(1H-imidazo[4,5-b]pyridin-2-ylthio)pentyloxy]phenoxy]-2,2-dimethylhexanoate as waxy solid.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 12 hours
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-519a95a668a94030af7035c3756cf998
Source dataset
uspto-grants-1990_01
Patent number
US04891432

Linked notes

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