Sodium Carbonate → HCID 67128330, compound

HRID 889661Notes

Reaction equation

HRID 889661 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20](OC)[C:19]=2[F:27])[CH2:8]/[C:9](=[N:12]\OS(C)(=O)=O)/[C:10]=1[Br:11])=[O:4].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.O>[CH3:1][O:2][C:3]([C:5]1[C:10]([Br:11])=[C:9]([NH2:12])[CH:8]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[F:27])[N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 178496865HCID 178496865, compound

Product 1

HCID 67128330HCID 67128330, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 3-bromo-6-(4-chloro-2-fluoro-3-methoxyphenyl)-4-[(E)-methylsulfonyloximino]-1,4,5,6-tetrahydropyridine-2-carboxylic acid methyl ester (23, 900 mg, 1.856 mmol) in glacial acetic acid (4.6 mL) was heated at 150° C. for 5 min in a Biotage microwave. After cooling to ambient temperature the reaction mixture was diluted with H2O and the pH was made neutral with a saturated solution of Na2CO3. The resulting mixture was extracted 3 times with ethyl acetate. The combined organic extracts were washed with brine, dried with Na2SO4, filtered and concentrated in vacuo. Silica gel column chromatography (20% EtOAc/pentane) gave 4-amino-3-bromo-6-(4-chloro-2-fluorophenyl)pyridine-2-carboxylic acid methyl ester (41; 0.60 g, 83%) as a light brown solid: mp 148-149° C.; 1H NMR (300 MHz, CDCl3) δ 7.65 (dd, J=8.6, 7.7 Hz, 1H), 7.26-7.20 (m, 1H), 7.14 (d, J=1.8 Hz, 1H), 4.91 (s, 2H), 3.99 (s, 3H), 3.97 (d, J=0.9 Hz, 3H); HRMS-ESI (m/z): calcd for C14H11BrClFN2O3, 387.962. found, 387.963.

Workup

  1. extractionThe resulting mixture was extracted 3 times with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee76bba9d6eb45208ef7ff8b6d111c92
Source dataset
uspto-grants-2012_08
Patent number
US08252938B2

Reaction notes

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