Dichloromethane → 6-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate

HRID 723500Notes

Reaction equation

HRID 723500 reaction equation
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7].[N:8]1C(C)=C[CH:11]=[CH:10][C:9]=1C.[F:16][C:17]([F:30])([F:29])[S:18]([O:21]S(C(F)(F)F)(=O)=O)(=[O:20])=[O:19].Cl[CH2:32]Cl>CN(C)C1C=CN=CC=1>[CH3:32][O:7][C:2]1[N:1]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:8]=[CH:9][CH:10]=[C:11]2[O:21][S:18]([C:17]([F:30])([F:29])[F:16])(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 79372,6-LutidineHCID 88712-PyridoneHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Pyridone (1a) (10 g, 0.057 mol) in dichloromethane (200 mL) containing 2,6-lutidine (9.94 mL, 0.086 mol) and 4-dimethylaminopyridine (0.07 g, 0.0057 mol) was cooled in ice and treated with trifluoromethanesulfonic anhydride (10.5 mL, 0.063 mol). After stirring for 2.5 hours the mixture was washed with saturated ammonium chloride solution, dried, evaporated and purified on silica gel (dichloromethane) to give a solid (13.2 g).

Workup

  1. temperaturewas cooled in ice
  2. washwas washed with saturated ammonium chloride solution
  3. customdried
  4. customevaporated
  5. custompurified on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-a1b0cb973a3f45d2a24d81f04f5030fe
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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