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Cesium carbonate → Methyl 4-((1-(4-(5-chloropyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate

HRID 1520251
ノート
印刷プレビュー

反応式

HRID 1520251 の反応式
[F:1][C:2]([F:34])([F:33])[CH2:3][CH2:4][CH:5]([NH:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)[C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:7]=1[CH3:21].[Cl:35][C:36]1[CH:37]=[N:38][C:39](I)=[N:40][CH:41]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.CN(C)C=O>[Cl:35][C:36]1[CH:37]=[N:38][C:39]([C:9]2[CH:10]=[CH:11][C:6]([CH:5]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:31][CH:32]=3)[CH2:4][CH2:3][C:2]([F:34])([F:33])[F:1])=[C:7]([CH3:21])[CH:8]=2)=[N:40][CH:41]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 299380055-Chloro-2-iodopyrimidineHCID 131733097Methyl 4-((4,4,4-trifluoro-1-(2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)amino)benzoate

生成物 1

HCID 117840298
Methyl 4-((1-(4-(5-chloropyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate
収率 60.4%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A reaction mixture of methyl 4-((4,4,4-trifluoro-1-(2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)amino)benzoate (7.85 g) obtained in Example 1, step F, 5-chloro-2-iodopyrimidine (4.35 g), tris(dibenzylideneacetone)dipalladium (0.753 g), 2,6-dimethoxy-2′-(dicyclohexylphosphino)biphenyl (1.35 g), cesium carbonate (16.08 g), dimethylformamide (65.8 mL) and water (16.5 ml) was stirred at 60° C. for 24 hr under a nitrogen atmosphere. The reaction mixture was added to saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) and washed with diethyl ether to give the title compound (4.61 g).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  6. washwashed with diethyl ether

出典と根拠

ORDレコード
ord-849b768d54b14d16bb20768b42f6484e
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073864B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート