Sodium Carbonate → HCID 67191235, compound

HRID 12254Notes

Reaction equation

HRID 12254 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[C:6]([N+:19]([O-:21])=[O:20])[C:5]=1[NH2:22].CC1C([N:31]2[C:36]([CH3:37])=[CH:35][C:34](OS(C(F)(F)F)(=O)=O)=[CH:33][C:32]2=O)=NC=CC=1.[C:47](=[O:50])([O-])[O-].[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:6]2[CH:5]=[C:4]([CH3:9])[CH:3]([CH2:37][C:36]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[C:47](=[O:50])[CH:7]=2)[CH:7]=[C:6]([N+:19]([O-:21])=[O:20])[C:5]=1[NH2:22]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 17984908N-(methyl-2-pyridinyl)-6-methyl-4-trifluoromethylsulfonyloxy-2-pyridoneHCID 59337633HCID 59337633, compound

Product 1

HCID 67191235HCID 67191235, compoundYield 175.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2-amino-3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (0.163 g, 0.51 mmol) in ethylene glycol dimethylether (5 mL) was added N-(methyl-2-pyridinyl)-6-methyl-4-trifluoromethylsulfonyloxy-2-pyridone (0.136 g, 0.41 mmol), bis(triphenylphoshine)palladium (II) dichloride (0.029 g, 0.04 mmol), and sodium carbonate (0.62 mL, 1.24 mmol of 2M). The resulting mixture was heated at reflux for 3 hours. After cooling and concentration in vacuo the resulting dark solid was purified (SiO2, 50% ethyl acetate/methylene chloride to 3% methanol in 50% ethyl acetate/methylene chloride) to provide the title compound as an orange solid (0.176 g, 89%). 1H NMR (500 MHz, CDCl3) δ 2.41 (s, 3H), 3.39 (s, 3H), 5.5 (s, 2H), 6.28 (s, 1H), 6.68 (s, 1H), 7.3-7.1 (m, 2H), 7.62 (t, 1H), 8.49 (s, 1H), 8.61 (s, 1H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. concentrationconcentration in vacuo the resulting dark solid
  5. customwas purified (SiO2, 50% ethyl acetate/methylene chloride to 3% methanol in 50% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-a1eedacf1b8549838884bd4e41b128f0
Source dataset
uspto-grants-2010_06
Patent number
US07727992B2

Reaction notes

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