Tetrabutylammonium Fluoride → 4-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-2,6-dipropyl-phenol

HRID 2399517Notes

Reaction equation

HRID 2399517 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[C:18]([CH2:20][CH2:21][CH3:22])[C:17]([O:23][Si](C(C)(C)C)(C)C)=[C:16]([CH2:31][CH2:32][CH3:33])[CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:34])[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:15]=[C:16]([CH2:31][CH2:32][CH3:33])[C:17]([OH:23])=[C:18]([CH2:20][CH2:21][CH3:22])[CH:19]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:34])[CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 193856855,7-dimethyl-2-ethyl-3-[4-tert-butyldimethylsilyloxy-3,5-dipropylphenyl]methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 193856864-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-2,6-dipropyl-phenolYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF solution of 5.0 g (10.44 mmol) of the product of Step F was treated with tetrabutylammonium fluoride (1.2 equiv, 1M solution in THF) overnight. THF was removed in vacuo and the residue was flash chromatographed using 30-50% ethyl acetate in hexane as eluent to afford 3.35 g (88%) of the title compound.

Workup

  1. customTHF was removed in vacuo
  2. customchromatographed

Sources & evidence

ORD record
ord-47bf0eaac35b48748344216d68d574ba
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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