Tetrabutylammonium Fluoride → [1-ethyl-3-(4-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]methyl acetate

HRID 587608Notes

Reaction equation

HRID 587608 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]2[N:30]([C:36]3[CH:41]=[CH:40][C:39]([O:42][Si](C(C)C)(C(C)C)C(C)C)=[CH:38][CH:37]=3)[C:31](=[O:35])[N:32]([CH2:33][CH3:34])[C:25]=12)(=[O:21])[CH3:20].[Cl-].[Cl-].[Ca+2]>C1COCC1>[C:19]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]2[N:30]([C:36]3[CH:37]=[CH:38][C:39]([OH:42])=[CH:40][CH:41]=3)[C:31](=[O:35])[N:32]([CH2:33][CH3:34])[C:25]=12)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 5284359Calcium ChlorideHCID 58577611[1-ethyl-2-oxo-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]methyl acetate

Product 1

HCID 58577626[1-ethyl-3-(4-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]methyl acetateYield 83.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.241 mL) was added to a solution of [1-ethyl-2-oxo-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]methyl acetate (300 mg) in THF (dry) (1 mL) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 30 min. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 20%-100% EtOAc in hexane) to give [1-ethyl-3-(4-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]methyl acetate (170 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography (silica gel, eluted with 20%-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-e6fc50d2b33f4121a5c3d90f420df4ad
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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