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Cesium fluoride → 4-Acetylamino-3-chloro-6-(2,4-difluoro-3-methylphenyl)-pyridine-2-carboxylic acid methyl ester

HRID 1782616
ノート
印刷プレビュー

反応式

HRID 1782616 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH3:9])[C:3]=1[F:10].[CH3:11][O:12][C:13]([C:15]1[C:20]([Cl:21])=[C:19]([NH:22][C:23](=[O:25])[CH3:24])[CH:18]=[C:17]([Sn](C)(C)C)[N:16]=1)=[O:14].C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F-].[Cs+]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][O:12][C:13]([C:15]1[C:20]([Cl:21])=[C:19]([NH:22][C:23](=[O:25])[CH3:24])[CH:18]=[C:17]([C:2]2[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH3:9])[C:3]=2[F:10])[N:16]=1)=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25953Cesium fluorideHCID 821241,4-Bis(diphenylphosphino)butaneHCID 112872263-Bromo-2,6-difluorotolueneHCID 226773084-Acetylamino-3-chloro-6-trimethylstannylpyridine-2-carboxylic acid methyl ester

生成物 1

HCID 685975834-Acetylamino-3-chloro-6-(2,4-difluoro-3-methylphenyl)-pyridine-2-carboxylic acid methyl ester収率 20%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

実験手順

A solution of 1-bromo-2,4-difluoro-3-methylbenzene (2.10 g, 0.09 mol), 4-acetylamino-3-chloro-6-trimethylstannylpyridine-2-carboxylic acid methyl ester (4.00 g, 0.01 mol), 1,4-bis(diphenylphosphino)butane (0.140 g, 0.0003 mol) and cesium fluoride (4.5 g, 0.03 mol) in acetonitrile (100 mL) was degassed with nitrogen. Palladium acetate (0.70 g, 0.0003 mol) was added the solution heated to reflux for 2 hours. The reaction mixture was filtered through celite and the filtrate diluted with water (200 mL) and then extracted with ethyl acetate (2×150 mL). The combined organic phases were dried and concentrated and the residual solid was purified by chromatography (50% ethyl acetate in hexanes) to give 4-acetylamino-3-chloro-6-(2,4-difluoro-3-methylphenyl)-pyridine-2-carboxylic acid methyl ester (0.800 g, 0.002 mol): mp 152-153° C.

後処理

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. additionthe filtrate diluted with water (200 mL)
  5. extractionextracted with ethyl acetate (2×150 mL)
  6. customThe combined organic phases were dried
  7. concentrationconcentrated
  8. customthe residual solid was purified by chromatography (50% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-100bc78c6db840f1b52b9e256a480b2c
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07498468B2

反応ノート

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