Ammonium Chloride → methyl (Z)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)-2-methoxyacrylate

HRID 390644ノート

反応式

HRID 390644 の反応式
[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:19][CH3:20])/[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][C:11]=1I)[CH2:2][CH2:3][CH3:4].[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:19][CH3:20])/[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][C:11]=1[C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([NH:22][CH3:21])[CH:24]=1)[CH2:2][CH2:3][CH3:4]

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 57976762N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59574929methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate

生成物 1

HCID 86626095methyl (Z)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)-2-methoxyacrylate収率 75.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 27342162-(Dicyclohexylphosphino)biphenyl触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
92.5 °C

実験手順

In a manner similar to that of Example 25c, 4 mg (0.018 mmol) of palladium acetate and then 13 mg (0.036 mmol) of 2-(dicyclohexylphosphino)biphenyl are added to a mixture of 0.7 g (1.8 mmol) of methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate prepared as in Example 24c, 0.5 g (2.15 mmol) of methyl[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]amine and 1.8 mL of aqueous 2M potassium phosphate solution in 10 mL of dimethylformamide. The reaction mixture is heated at 90-95° C. for 1 hour. The reaction medium is hydrolyzed with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over magnesium sulfate. The solvent is evaporated off and the residue is purified by chromatography on a column of silica eluted with a 60/40 heptane/ethyl acetate mixture. 0.5 g (71%) of methyl (Z)-3-(2-butoxy-3′-methylaminobiphenyl-4-yl)-2-methoxyacrylate are obtained.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent is evaporated off
  5. customthe residue is purified by chromatography on a column of silica
  6. washeluted with a 60/40 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-35d8bb8ca66142369a1fd4caa4ac6cce
出典データセット
uspto-grants-2013_02
特許番号
US08383652B2

反応ノート

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