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

HRID 421888ノート

反応式

HRID 421888 の反応式
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

参加物

6

反応物 4

HCID 887MethanolHCID 10942334Sodium Methoxide2 回HCID 666734732-(4-Bromo-2-fluorophenylamino)-6-methoxy-nicotinic acid methyl esterHCID 866723242-(4-Bromo-2-fluorophenylamino)-6-chloro-nicotinic acid methyl ester

生成物 1

HCID 576368232-(4-Bromo-2-fluorophenylamino)-6-oxo-1,6-dihydropyridine-3-carboxylic acid収率 88%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
62.5 °C

実験手順

Preparation of 2-(4-bromo-2-fluorophenylamino)-6-methoxynicotinic acid methyl ester: To a mixture of 2-(4-bromo-2-fluorophenylamino)-6-chloronicotinic 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 at 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.

後処理

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

出典と根拠

ORDレコード
ord-0013aaad9b304465a32d13e3ff7c45e0
出典データセット
uspto-grants-2012_01
特許番号
US08101611B2

反応ノート

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