Pyridine → HCID 23631099, compound

HRID 917699Notes

Reaction equation

HRID 917699 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:6]([C:13]([OH:15])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1.N1C=CC=CC=1.FC(F)(F)C(O[C:32]1[C:37]([F:38])=[C:36]([F:39])[C:35]([F:40])=[C:34]([F:41])[C:33]=1[F:42])=O>CC(N(C)C)=O.CCOC(C)=O>[F:1][C:2]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:6]([C:13]([O:15][C:32]2[C:33]([F:42])=[C:34]([F:41])[C:35]([F:40])=[C:36]([F:39])[C:37]=2[F:38])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 112346084-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

Product 1

HCID 23631099HCID 23631099, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent2×

Procedure

4-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid (894 mg, 2.30 mmol) and pyridine (909 mg, 11.5 mmol) were dissolved in DMA (15 mL). To this mixture was added pentafluorophenyl trifluoroacetate (3.22 g, 11.5 mmol) then the solution was allowed to stir at R.T. for 2 h. The DMA solution was diluted with EtOAc (150 mL), which was washed sequentially with 1 M HCl (2×100 mL), water (100 mL), sat. NaHCO3 (2×100 mL), and brine (100 mL). The EtOAc fraction was then dried (Na2SO4) and the solvent removed under reduced pressure to yield a viscous oil which was purified by column chromatography on silica gel (50% EtOAc/PE as eluant). This afforded 2,3,4,5,6-pentafluorophenyl-4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate as a cream foam (1.22 g, 96%) which was used directly in subsequent steps. 1H NMR [(CD3)2SO, 400 MHz] δ 9.03 (s, 1H), 8.70 (s, 1H), 7.79 (dd, J=10.1, 1.9 Hz, 1H), 7.62 (br dd, J=8.4, 1.0 Hz, 1H), 7.29 (t, J=8.4 Hz, 1H), 5.36 (d, J=1.6 Hz, 1H), 3.45 (s, 3H). LCMS (APCI+) calcd for C19H9F6N2O3 555 (MH+), found 555.

Workup

  1. washwas washed sequentially with 1 M HCl (2×100 mL), water (100 mL), sat. NaHCO3 (2×100 mL), and brine (100 mL)
  2. dry with materialThe EtOAc fraction was then dried (Na2SO4)
  3. customthe solvent removed under reduced pressure
  4. customto yield a viscous oil which
  5. customwas purified by column chromatography on silica gel (50% EtOAc/PE as eluant)

Sources & evidence

ORD record
ord-7e7dc2d8cfb3478781a7ecd2dc22155d
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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