Trifluoroacetic acid → HCID 71114811, compound

HRID 1624035Notes

Reaction equation

HRID 1624035 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:16][CH2:15][CH2:14][C:13]3[C:9]2=[CH:10][N:11]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[N:12]=3)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:13]([CH2:14][CH2:15][CH:16]=2)=[N:12][N:11]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:10]=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 71114884HCID 71114884, compound

Product 1

HCID 71114811HCID 71114811, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Chlorophenyl)-2-(p-tolylsulfonyl)-6,7-dihydro-5H-indazol-4-ol (0.76 g, 1.89 mmol) is added to dichloromethane (20.0 mL), triethylsilane (6.04 mL, 37.7 mmol), and TFA (0.16 mL, 2.07 mmol) and stirred at room temperature for 2.0 h. The reaction is quenched with saturated NaHCO3, separated, the organics washed with brine dried over Na2SO4, filtered, and evaporated to dryness to give the title compound (0.622 g, 86%). 1H NMR (CDCl3) δ 2.42 (s, 3H), 2.55 (m, 2H), 2.82 (t, 2H), 5.98 (t, 1H), 7.37-7.31 (m, 6H), 7.81 (s, 1H), 7.87 (d, 2H).

Workup

  1. customThe reaction is quenched with saturated NaHCO3
  2. customseparated
  3. washthe organics washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-c509ac799213458386417c403b5ae4fd
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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