Potassium Phosphate, Tribasic → ethyl (E)-3-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methylacrylate

HRID 390660ノート

反応式

HRID 390660 の反応式
[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[CH3:20])/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][C:11]=1I)[CH2:2][CH2:3][CH3:4].[CH3:21][N:22]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:24].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.[Cl-].[NH4+].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](\[CH3:20])/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][C:11]=1[C:33]1[CH:34]=[CH:35][CH:36]=[C:31]([N:22]([CH3:21])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:24])[CH:32]=1)[CH2:2][CH2:3][CH3:4]

参加物

8

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 672732723-(1-Methyl-3-pentylureido)phenylboronic acidHCID 86626086ethyl (E)-3-(3-butoxy-4-iodophenyl)-2-methylacrylate

生成物 1

HCID 86626104ethyl (E)-3-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methylacrylate収率 85.3%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 27342162-(Dicyclohexylphosphino)biphenyl触媒HCID 6228Dimethylformamide溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
92.5 °C

実験手順

3 mg (0.013 mmol) of palladium acetate and then 9 mg (0.026 mmol) of 2-(dicyclohexylphosphino)biphenyl are added to a mixture of 505 mg (1.3 mmol) of ethyl (E)-3-(3-butoxy-4-iodophenyl)-2-methylacrylate prepared as described in Example 19h, 446 mg (1.7 mmol) of 3-(1-methyl-3-pentylureido)phenylboronic acid prepared as described in Example 24h and 1.3 mL of aqueous 2 M potassium phosphate solution in 6.5 mL of dimethylformamide. The reaction mixture is heated at 90-95° C. for 2 hours. The reaction medium is hydrolyzed in saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. After filtration, the solvent is evaporated off and the brown oil obtained (1.5 g) is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture. 533 mg (85%) of ethyl (E)-3-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methylacrylate are obtained.

後処理

  1. customprepared
  2. customprepared
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent is evaporated off
  8. customthe brown oil obtained (1.5 g)
  9. customis purified by chromatography on a column of silica
  10. washeluted with a 70/30 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-7ad05b2ecb41461d972747008f1fb3dc
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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