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

HRID 1492607Notes

Reaction equation

HRID 1492607 reaction equation
[Si]([O:8][C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:12]([CH2:18][N:19]2[C:23]3=[N:24][C:25]([CH3:29])=[CH:26][C:27]([CH3:28])=[C:22]3[N:21]=[C:20]2[CH2:30][CH3:31])=[CH:11][C:10]=1[CH2:32][CH2:33][CH3:34])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:29][C:25]1[N:24]=[C:23]2[N:19]([CH2:18][C:12]3[CH:11]=[C:10]([CH2:32][CH2:33][CH3:34])[C:9]([OH:8])=[C:14]([CH2:15][CH2:16][CH3:17])[CH:13]=3)[C:20]([CH2:30][CH3:31])=[N:21][C:22]2=[C:27]([CH3:28])[CH:26]=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-163803fb25a8419e815f112edfd08429
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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