Acetic Acid → 4-(4-Bromo-2-fluorophenylamino)-5-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester

HRID 2111071Notes

Reaction equation

HRID 2111071 reaction equation
Br.[CH3:2][O:3][C:4](=[O:23])[C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[F:19])=[C:9]([F:20])[C:8]([O:21]C)=[N:7][CH:6]=1.C(O)(=O)C>O>[CH3:2][O:3][C:4]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[F:19])=[C:9]([F:20])[C:8](=[O:21])[NH:7][CH:6]=1)=[O:23]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 666740814-(4-Bromo-2-fluorophenylamino)-5-fluoro-6-methoxy-nicotinic acid methyl ester

Product 1

HCID 666735074-(4-Bromo-2-fluorophenylamino)-5-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl esterYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Hydrobromic acid (5.82 mL, 51.5 mmol) was added to a mixture of 4-(4-bromo-2-fluorophenylamino)-5-fluoro-6-methoxy-nicotinic acid methyl ester (0.64 g, 1.72 mmol) and acetic acid (5.9 mL, 103 mmol). The reaction mixture was stirred at 90° C. for 20 minutes and then cooled to room temperature. After water was added to the mixture, a white precipitate formed. The white solid was collected by filtered and washed with water and diethyl ether to yield 0.60 g (97%) clean desired product.

Workup

  1. temperaturecooled to room temperature
  2. customa white precipitate formed
  3. customThe white solid was collected
  4. filtrationby filtered
  5. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-747a242a007e41a68da491ea9b0b120e
Source dataset
uspto-grants-2009_04
Patent number
US07517994B2

Reaction notes

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