Water → methyl (Z)-3-(3'-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate

HRID 390692

반응식

HRID 390692 반응식
C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1.[CH2:18]([O:22][C:23]1[CH:24]=[C:25](/[CH:30]=[C:31](\[O:36][CH3:37])/[C:32]([O:34][CH3:35])=[O:33])[CH:26]=[CH:27][C:28]=1I)[CH2:19][CH2:20][CH3:21].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[NH2:8][C:9]1[CH:10]=[C:11]([C:28]2[CH:27]=[CH:26][C:25](/[CH:30]=[C:31](\[O:36][CH3:37])/[C:32]([O:34][CH3:35])=[O:33])=[CH:24][C:23]=2[O:22][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:13][CH:14]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27632413-Aminophenylboronic acid hydrochlorideHCID 59574929methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate

생성물 1

HCID 86626122methyl (Z)-3-(3'-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate수율 93.8%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

11.2 mL (22.4 mmol) of aqueous 2 N potassium carbonate solution and 0.52 g (0.45 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution of 1.87 g (10.8 mmol) of 3-aminophenylboronic acid hydrochloride and 3.5 g (9 mmol) of methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate (prepared according to Example 24c) in 70 mL of ethylene glycol dimethyl ether. The reaction mixture is heated at 100° C. for 4 hours. After addition of 30 mL of water and extraction with ethyl acetate, the organic phases are combined, washed with saturated sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 3 g (93%) of methyl (Z)-3-(3′-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate are obtained in the form of a yellow oil.

후처리

  1. washwashed with saturated sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then purified by chromatography on a column of silica
  5. washeluted with a 90/10 heptane/ethyl acetate mixture

출처 및 근거

ORD 기록
ord-4f9266252fc34994bf2d41c1de451922
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383652B2

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