Pyridine → 6-trifluoromethanesulfonyloxy-5-methoxycarbonyl-3-phenyl-3-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyran

HRID 2369642Notes

Reaction equation

HRID 2369642 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].O[C:17]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:20]2[O:21][CH2:22][C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:27][CH:26]=3)[CH:24]=[C:19]2[C:18]=1[C:48]([O:50][CH3:51])=[O:49].N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:20]2[O:21][CH2:22][C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:27][CH:26]=3)[CH:24]=[C:19]2[C:18]=1[C:48]([O:50][CH3:51])=[O:49])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 67162696Methyl 6-hydroxy-3-phenyl-3-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyran-5-carboxylate

Product 1

HCID 866536106-trifluoromethanesulfonyloxy-5-methoxycarbonyl-3-phenyl-3-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyranYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (5.32 g, 18.9 mmol) was added dropwise to a solution of 6-hydroxy-5-methoxycarbonyl-3-phenyl-3-(4-pyrrolidinophenyl)-2H-naphtho-[1,2-b]pyran (4.8 g, 10 mmol) and pyridine (1.7 g, 21.6 mmol) in DCM (100 mL) at 0° C. under N2 with stirring. After 1 h the resulting solution was washed with HCl (100 mL, 2 M), water (100 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM as eluent. The solvent was removed under reduced pressure to give the title compound (3.57 g, 58%) as a blue powder.

Workup

  1. washAfter 1 h the resulting solution was washed with HCl (100 mL, 2 M), water (100 mL)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. filtrationThe residue was filtered through a short plug of silica
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c78cde626953446fb7ef64b5b3769ce6
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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