Pyridine → Trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-8-methoxy-4-oxo-4H-chromen-7-yl ester

HRID 14467

Reaction equation

HRID 14467 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:32](=[O:33])[C:31]3[C:26](=[C:27]([O:35][CH3:36])[C:28]([O-])=[CH:29][CH:30]=3)[O:25][C:24]=2[CH:37]([CH3:39])[CH3:38])=[CH:19][CH:18]=1.[Na+].ClC1C=CC(C2C(=O)C3C(=C(OC)C(O)=CC=3)OC=2C(C)C)=CC=1.[H-].[Na+].N1C=CC=CC=1>C(Cl)Cl.O1CCCC1.CN(C)C1C=CN=CC=1>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:32](=[O:33])[C:31]3[C:26](=[C:27]([O:35][CH3:36])[C:28]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:29][CH:30]=3)[O:25][C:24]=2[CH:37]([CH3:39])[CH3:38])=[CH:21][CH:22]=1

Participants

9

Reactant 5

HCID 1049PyridineHCID 24758Sodium hydrideHCID 67749Trifluoromethanesulfonic anhydrideHCID 116026403-(4-Chlorophenyl)-7-hydroxy-2-isopropyl-8-methoxy-chromen-4-oneHCID 68702553sodium 3-(4-chlorophenyl)-2-isopropyl-8-methoxy-4-oxo-4H-chromen-7-olate

Product 1

HCID 86625609Trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-8-methoxy-4-oxo-4H-chromen-7-yl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trifluoromethanesulfonic acid anhydride (3.5 g, 2.1 ml, 12.4 mmol, 2 eq.) in anhydrous methylene chloride (10 ml) is added dropwise to a stirred solution of sodium 3-(4-chlorophenyl)-2-isopropyl-8-methoxy-4-oxo-4H-chromen-7-olate (2.28 g, 6.22 mmol; prepared by treating 3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-8-methoxy-chromen-4-one with a molar equivalent of sodium hydride in dry tetrahydrofuran), pyridine (2 g, 2.1 ml, 25.5 mmol, 4.1 eq.) and 4-dimethylaminopyridine (0.076 g, 0.62 mmol, 0.1 eq.) in anhydrous methylene chloride (60 ml) at 0° C. After stirring overnight, the solution is washed with 1M HCl solution. The organic phase is dried over anhydrous magnesium sulfate and filtered, and the solvent is removed by evaporation in vacuo to afford the title compound as a brown foam. The product is used in the next step without further purification.

Workup

  1. customprepared
  2. washthe solution is washed with 1M HCl solution
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is removed by evaporation in vacuo

Sources & evidence

ORD record
ord-05226ec6f4434c27aabeb6b088529016
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Linked notes

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