(Trifluoromethyl)trimethylsilane → HCID 57377969, compound

HRID 218212Notes

Reaction equation

HRID 218212 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[N:21]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[N:22]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:30]([Si](C)(C)C)([F:33])([F:32])[F:31].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCOC(C)=O>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([C:1]([OH:3])([CH3:2])[C:30]([F:33])([F:32])[F:31])=[CH:9][CH:8]=2)(=[O:12])=[O:11])=[C:15]([N:21]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[N:22]2)[CH:16]=1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 573784044-acetyl-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)benzenesulfonamide

Product 1

HCID 57377969HCID 57377969, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 4-acetyl-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)-benzene-sulfonamide (synthesized according to general procedures F and G, 500 mg, 1.17 mmol) was added CF3-TMS (trifluoromethyl-trimethylsilane) (4.7 mL, 0.5 M solution in THF), followed by TBAF (tetra-n-butylammonium fluoride) (2.34 mL, 1.0 M solution in THF) at 0° C., and the solution was stirred at room temperature for 16 hours. Both TLC and LCMS analysis indicated ˜10-15% completion of reaction. The reaction mixture was diluted with EtOAc (50 mL) and the organics were washed with washed with 2 N HCl (2×25 mL), water (25 mL), and brine (25 mL). The organics were subsequently dried (Na2SO4), concentrated in vacuo, and purified by automated flash chromatography followed by preparative HPLC to afford the title compound as a white powder: MS (ES) M+H expected 498.1, found 498.0.

Workup

  1. custom˜10-15% completion of reaction
  2. washthe organics were washed
  3. washwith washed with 2 N HCl (2×25 mL), water (25 mL), and brine (25 mL)
  4. dry with materialThe organics were subsequently dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by automated flash chromatography

Sources & evidence

ORD record
ord-e84ea3eb6e3f4e04b2319103f4348481
Source dataset
uspto-grants-2012_06
Patent number
US08198309B2

Reaction notes

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