Nitrogen → Trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)benzoyl]-naphthalen-2-yl ester

HRID 732802Notes

Reaction equation

HRID 732802 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:18][CH:17]=1)=[O:15].N#N.N1C=CC=CC=1.[F:39][C:40]([F:46])([F:45])[S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3]([C:14](=[O:15])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:18][CH:17]=1)=[C:2]([O:1][S:41]([C:40]([F:46])([F:45])[F:39])(=[O:43])=[O:42])[CH:11]=[CH:10]2

Participants

6

Reactant 4

HCID 947NitrogenHCID 1049PyridineHCID 79000Trifluoromethanesulfonyl chlorideHCID 219316286-Methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-ol

Product 1

HCID 11685250Trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)benzoyl]-naphthalen-2-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone in CH2Cl2 (10 volumes) in a three neck round bottom flask equipped with a stir bar and N2 source and chill to 0° C. in an ice/brine bath. Add pyridine (1.3 eq.). Add trifluoromethanesulfonyl chloride (1.2 eq.) via syringe over 15 minutes. After about 15 minutes, quench the reaction with H2O (10 volumes), wash with 1 N aqueous HCl (5 volumes) and 1.0 N aqueous NaHCO3, and dry over Na2SO4. Obtain the title compound in quantitative yield after concentration.

Workup

  1. customequipped with a stir bar
  2. customquench
  3. customthe reaction with H2O (10 volumes)
  4. washwash with 1 N aqueous HCl (5 volumes) and 1.0 N aqueous NaHCO3
  5. dry with materialdry over Na2SO4

Sources & evidence

ORD record
ord-10f401f051734b89b26c96af279a0449
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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