Tetrabutylammonium Fluoride → N-{[4-(hydroxymethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide

HRID 607427Notes

Reaction equation

HRID 607427 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:44])(=[O:43])=[N:17][C:18](=[O:42])[C:19]2[CH:24]=[C:23]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]4[O:37][CH:38]=[CH:39][C:40]=4[CH3:41])=[O:35])[CH:28]=3)[CH:22]=[N:21][CH:20]=2)=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:44])(=[O:43])=[N:17][C:18](=[O:42])[C:19]2[CH:24]=[C:23]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]4[O:37][CH:38]=[CH:39][C:40]=4[CH3:41])=[O:35])[CH:28]=3)[CH:22]=[N:21][CH:20]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57657965N-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl](methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide

Product 1

HCID 57657893N-{[4-(hydroxymethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamideYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl](methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide (0.722 g, 1.15 mmol) was dissolved in THF (2.3 mL). The resulting solution was treated with 1M solution of TBAF in THF (2.3 mL, 2.30 mmol) causing the mixture to turn black in color. The mixture was allowed to stir for 1 h, subsequently dissolved in EtOAc (10 mL) and extracted with H2O (3×15 mL). The organic layer was dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The crude product was purified via column chromatography (gradient eluant mixture of EtOAc in Hexanes: 0% to 100% EtOAc) to afford the title compound in 94% yield (0.350 g, 0.682 mmol).

Workup

  1. extractionextracted with H2O (3×15 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4(s)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified via column chromatography (gradient eluant mixture of EtOAc in Hexanes: 0% to 100% EtOAc)

Sources & evidence

ORD record
ord-eeee594599414b9285630070c5275b2b
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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