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

HRID 704358Notes

Reaction equation

HRID 704358 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-bfef365c482c4a288f18424a0c419884
Source dataset
uspto-grants-1991_01
Patent number
US04987147

Reaction notes

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