Methanol → 2-(4-Bromo-2-fluorophenylamino)-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 1510508Notes

Reaction equation

C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10]C)=[N:6][C:5]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[F:20].COC(=O)C1C=CC(Cl)=NC=1NC1C=CC(Br)=CC=1F.C[O-].[Na+].CO>C(O)(=O)C>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:5]2[NH:6][C:7](=[O:10])[CH:8]=[CH:9][C:4]=2[C:3]([OH:21])=[O:2])=[C:14]([F:20])[CH:15]=1

Participants

Conditions

Temperature: 62.5 °C

Procedure

Preparation of 2-(4-bromo-2-fluorophenylamino)-6-methoxy-nicotinic acid methyl ester: To a mixture of 2-(4-bromo-2-fluorophenylamino)-6-chloro-nicotinic acid methyl ester (2.00 g, 5.56 mmol) and sodium methoxide (0.791 g, 13.9 mmol) was added MeOH (50 mL) to give a slurry that was stirred al 60-65° C. for 16 hours under N2. Additional sodium methoxide (0.791 g, 13.9 mmol) was added and the reaction mixture was allowed to stir another 3 days at 60-65° C. The reaction mixture was cooled to room temperature and glacial acetic acid was added dropwise until the pH was 7. The resulting suspension was filtered and washed with H2O to yield a pink solid that was collected and dried under vacuum to yield 1.74 g (88%) pure desired product.

Workup

customto give a slurry that
stirringto stir another 3 days at 60-65° C
temperatureThe reaction mixture was cooled to room temperature
filtrationThe resulting suspension was filtered
washwashed with H2O
customto yield a pink solid
customthat was collected
customdried under vacuum

Sources & evidence

ORD record: ord-b8702786feee405ca622c89004cd3150
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211920B2

Reaction notes

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