Pyridine → HCID 86613923, compound

HRID 504009Notes

Reaction equation

HRID 504009 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].[C:22]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:27]=[CH:26][C:25]([CH2:28][N:29]2[C:38]3[C:33](=[C:34](O)[CH:35]=[CH:36][C:37]=3[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:32][CH2:31][C:30]2=[O:46])=[CH:24][CH:23]=1>ClCCl>[C:22]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:27]=[CH:26][C:25]([CH2:28][N:29]2[C:38]3[C:33](=[C:34]([O:12][S:9]([C:8]([F:21])([F:20])[F:7])(=[O:11])=[O:10])[CH:35]=[CH:36][C:37]=3[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:32][CH2:31][C:30]2=[O:46])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 66596773HCID 66596773, compound

Product 1

HCID 86613923HCID 86613923, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (1.12 ml) and trifluoromethanesulfonic anhydride (1.99 ml) were added with stirring at 0° C. to an anhydrous dichloromethane solution (40 ml) of 1-(biphenyl-4-ylmethyl)-5-hydroxy-8-phenyl-3,4-dihydro-1H-quinolin-2-one (4.0 g), followed by stirring for 1 hour. The resulting mixture was concentrated under reduced pressure, water was added to the residue, and extraction with dichloromethane was performed. The extract was washed with water, an aqueous potassium hydrogensulfate solution and water in this order, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to thereby obtain 5.45 g (yield: quantitative) of 1-(biphenyl-4-ylmethyl)-8-phenyl-5-trifluoromethanesulfonyloxy-3,4-dihydro-1H-quinolin-2-one as a white amorphous solid.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue, and extraction with dichloromethane
  3. washThe extract was washed with water
  4. dry with materialan aqueous potassium hydrogensulfate solution and water in this order, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c518006378b04e7e997ab91830c3acc4
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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