Ammonium Chloride → ethyl (E)-3-[2-butoxy-3'-(1-methyl-3-heptylureido)biphenyl-4-yl]-2-methylacrylate

HRID 390663노트

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HRID 390663 반응식
[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].[CH2:21]([NH:28][C:29](=[O:47])[N:30]([CH3:46])[C:31]1[CH:36]=[CH:35][CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].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](\[CH3:20])/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][C:11]=1[C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([N:30]([CH3:46])[C:29]([NH:28][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:47])[CH:36]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 595749253-Heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]ureaHCID 86626086ethyl (E)-3-(3-butoxy-4-iodophenyl)-2-methylacrylate

생성물 1

HCID 86626105ethyl (E)-3-[2-butoxy-3'-(1-methyl-3-heptylureido)biphenyl-4-yl]-2-methylacrylate수율 84.4%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 27342162-(Dicyclohexylphosphino)biphenyl촉매HCID 6228Dimethylformamide용매

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온도
92.5 °C

실험 절차

In a manner similar to that of Example 34a, 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, 494 mg (1.7 mmol) of 3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]urea 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 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 brown oil obtained (1.3 g) is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture. 558 mg (84%) of ethyl (E)-3-[2-butoxy-3′-(3-heptyl-1-methyl-ureido)biphenyl-4-yl]-2-methylacrylate are obtained.

후처리

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is evaporated off
  6. customthe brown oil obtained (1.3 g)
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 70/30 heptane/ethyl acetate mixture

출처 및 근거

ORD 기록
ord-083bf2888ae44801bfe1da2848ea4a26
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383652B2

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