Trifluoroacetic acid → HCID 25074011, compound

HRID 884344Notes

Reaction equation

HRID 884344 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[CH:20]=[CH2:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:22]([N:29]([CH2:35]OC)[CH2:30][Si](C)(C)C)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:22]([N:29]1[CH2:35][CH2:21][CH:20]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[N:12]=[CH:11][C:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:8])=[O:9])=[CH:19]3)[CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 66854566HCID 66854566, compound

Product 1

HCID 25074011HCID 25074011, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Phenylsulfonyl)-8-vinylquinoline (210 mg, 0.71 mmol, prepared according to WO2007039219) was reacted with benzyl methoxymethyl trimethylsilylmethyl amine (253 mg, 1.07 mmol) in dichloromethane (2 ml) in the presence of trifluoroacetic acid for 20 minutes. The solution was washed with a saturated aqueous solution of NaHCO3 solution, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by chromatography (100% dichloromethane) to give the title compound as a colourless oil (100 mg, 33%).

Workup

  1. washThe solution was washed with a saturated aqueous solution of NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (100% dichloromethane)

Sources & evidence

ORD record
ord-800ff582fff2438fb4ef0aa015761757
Source dataset
uspto-grants-2012_08
Patent number
US08242102B2

Reaction notes

Loading…