Pyridine → HCID 59575351, compound

HRID 1468598Notes

Reaction equation

HRID 1468598 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].[CH:16]1[C:25]2[C:20](=[C:21]3[CH:33]=[CH:32][CH:31]=[CH:30][C:22]3=[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]3=2)[CH:19]=[C:18](O)[N:17]=1.N1C=CC=CC=1>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:18]1[N:17]=[CH:16][C:25]2[C:20]([CH:19]=1)=[C:21]1[CH:33]=[CH:32][CH:31]=[CH:30][C:22]1=[C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=21)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178515295HCID 178515295, compound

Product 1

HCID 59575351HCID 59575351, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (5.2 g, 19 mmol) was added to a mixture of dibenzo[f,h]isoquinolin-3-ol (0.91 g, 3.7 mmol), pyridine (1.2 g, 15 mmol) and dichloromethane 100 mL under nitrogen at 0° C. and stirred overnight at room temperature. The reaction was quenched with saturated NaHCO3. The organic layer was washed with water and dried on Na2SO4. The residue was purified by flash chromatography on silica (hexane:ethyl acetate) to give (1.1 g, 79%).

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. washThe organic layer was washed with water
  3. customdried on Na2SO4
  4. customThe residue was purified by flash chromatography on silica (hexane:ethyl acetate)
  5. customto give (1.1 g, 79%)

Sources & evidence

ORD record
ord-4570cbe0f1414894a424a82ba30e0d69
Source dataset
uspto-grants-2015_04
Patent number
US09005771B2

Reaction notes

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