Water → HCID 118534015, compound

HRID 1497378Notes

Reaction equation

HRID 1497378 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:19]([CH3:20])=[C:18]2[C:13]([CH:14]=[CH:15][C:16]([N:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)=[CH:23][C:22]3=[O:36])=[CH:17]2)=[N:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][O:27][C:24]2[CH:25]=[CH:26][N:21]([C:16]3[CH:15]=[CH:14][C:13]4[C:18](=[C:19]([CH3:20])[N:11]([CH2:10][CH2:9][OH:8])[N:12]=4)[CH:17]=3)[C:22](=[O:36])[CH:23]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131734201HCID 131734201, compound

Product 1

HCID 118534015HCID 118534015, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-methyl-2H-indazol-5-yl]-4-[(4-chlorobenzyl)oxy]pyridin-2(1H)-one (295 mg) in tetrahydrofuran (5 ml) was added tetra-n-butylammonium fluoride (1 M tetrahydrofuran solution, 1.13 ml) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) to give the title compound (221 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol)

Sources & evidence

ORD record
ord-d2003def9d114ff9b970703c386322b0
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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