Cesium fluoride → 4-Acetylamino-3-chloro-6-(4-chloro-2-fluoro-5-methoxyphenyl)pyridine-2-carboxylic acid methyl ester

HRID 2249388

反応式

HRID 2249388 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:8]=[C:7](Cl)[N:6]=1)=[O:4].[Cl:17][C:18]1[C:23]([O:24][CH3:25])=[CH:22][C:21](B2OCCCO2)=[C:20]([F:32])[CH:19]=1.[F-].[Cs+].C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:8]=[C:7]([C:21]2[CH:22]=[C:23]([O:24][CH3:25])[C:18]([Cl:17])=[CH:19][C:20]=2[F:32])[N:6]=1)=[O:4]

参加物

8

反応物 4

HCID 25953Cesium fluorideHCID 821241,4-Bis(diphenylphosphino)butaneHCID 22677481Methyl 4-acetamido-3,6-dichloropyridine-2-carboxylateHCID 669547012-(4-Chloro-2-fluoro-5-methoxyphenyl)-[1,3,2]-dioxaborinane

生成物 1

HCID 686005934-Acetylamino-3-chloro-6-(4-chloro-2-fluoro-5-methoxyphenyl)pyridine-2-carboxylic acid methyl ester収率 75%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

A solution of 4-acetylamino-3,6-dichloropyridine carboxylic acid methyl ester (4.3 g, 0.016 mol), 2-(4-chloro-2-fluoro-5-methoxyphenyl)-[1,3,2]-dioxaborinane (4.5 g, 0.018 mol), cesium fluoride (3.5 g, 0.025 mol), and 1,4-bis(diphenylphosphino)butane (0.360 g, 0.0016 mol) in acetonitrile (100 mL) was degassed with nitrogen for 15 minutes before palladium acetate (0.180 g, 0.0016 mol) was added and the solution heated under reflux for 18 hours. Water (150 mL) was added and the resulting solid collected and dried to give 4-acetylamino-3-chloro-6-(4-chloro-2-fluoro-5-methoxyphenyl)pyridine-2-carboxylic acid methyl ester (4.5 g, 0.012 mol): mp 180-182° C.

後処理

  1. additionwas added
  2. temperaturethe solution heated
  3. temperatureunder reflux for 18 hours
  4. customthe resulting solid collected
  5. customdried

出典と根拠

ORDレコード
ord-3afd6bd59fae4532bce4e1eba2f0e7dc
出典データセット
uspto-grants-2008_01
特許番号
US07314849B2

関連ノート

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