Potassium Phosphate, Tribasic → Ethyl 2-[1-(2-ethoxy-3'-methylaminobiphenyl-4-yl)meth-(e)-ylidene]butyrate

HRID 390658ノート

反応式

HRID 390658 の反応式
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[CH2:26]([O:28][C:29]1[CH:30]=[C:31](/[CH:43]=[C:44](\[CH2:50][CH3:51])/[C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:32]=[CH:33][C:34]=1OS(C(F)(F)F)(=O)=O)[CH3:27].[CH3:52][NH:53][C:54]1[CH:59]=[CH:58][CH:57]=[C:56](B2OC(C)(C)C(C)(C)O2)[CH:55]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.[Cl-].[NH4+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:26]([O:28][C:29]1[CH:30]=[C:31](/[CH:43]=[C:44](\[CH2:50][CH3:51])/[C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:32]=[CH:33][C:34]=1[C:56]1[CH:57]=[CH:58][CH:59]=[C:54]([NH:53][CH3:52])[CH:55]=1)[CH3:27]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 57976762N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 87636882Ethyl 2-[1-(3-ethoxy-4-trifluoromethanesulfonyloxyphenyl)meth-(e)-ylidene]butyrate

生成物 1

HCID 68957253Ethyl 2-[1-(2-ethoxy-3'-methylaminobiphenyl-4-yl)meth-(e)-ylidene]butyrate収率 37.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
92.5 °C

実験手順

45 mg (0.2 mmol) of palladium acetate and then 140 mg (0.4 mmol) of 2-(dicyclohexylphosphino)biphenyl are added to a mixture of 1.7 g (4 mmol) of ethyl 2-[1-(3-ethoxy-4-trifluoromethanesulfonyloxyphenyl)meth-(E)-ylidene]butyrate, 1.1 g (4.8 mmol) of methyl[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]amine (prepared according to Example 28a) and 2 mL of aqueous 2 M potassium phosphate solution in 8 mL of dimethylformamide. The reaction mixture is heated at 90-95° C. for 3 hours. The reaction medium is hydrolyzed in saturated ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent is evaporated off and the brown oil obtained (2.3 g) is purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 526 mg (15%) of ethyl 2-[1-(2-ethoxy-3′-methylaminobiphenyl-4-yl)meth-(E)-ylidene]butyrate are obtained in the form of a yellow oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is evaporated off
  5. customthe brown oil obtained (2.3 g)
  6. customis purified by chromatography on a column of silica
  7. washeluted with a 90/10 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-af62b1e9ce644f949c32c41dacb2c043
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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