4-Aminophenylboronic acid → 3-(4'-Amino-biphenyl-4-carbonyl)-cyclohexanecarboxylic acid methyl ester

HRID 907704노트

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HRID 907704 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)[CH2:6]1)=[O:4].[NH2:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]([C:12]2[CH:17]=[CH:16][C:15]([C:24]3[CH:25]=[CH:26][C:21]([NH2:20])=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)=[O:19])[CH2:6]1)=[O:4]

참가 물질

6

반응물 2

HCID 27346154-Aminophenylboronic acidHCID 235493383-(4-Bromo-benzoyl)cyclohexanecarboxylic acid methyl ester

생성물 1

HCID 235493393-(4'-Amino-biphenyl-4-carbonyl)-cyclohexanecarboxylic acid methyl ester

시약·촉매·용매 3

HCID 1140Toluene용매HCID 10340Sodium Carbonate용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a solution of 3-(4-bromo-benzoyl)cyclohexanecarboxylic acid methyl ester (500 mg, 1.54 mmol) and 4-aminophenyl boronic acid (252 mg, 1.85 mmol) in toluene (40 mL) and dioxane (10 mL), 2 N aqueous Na2CO3 (10 mL) was added, and the mixture was degassed by bubbling with a flow of argon for 45 minutes. (1,1-Bis(diphenylphosphino)ferrocene)-dichloropalladium (63 mg, 0.08 mmol) was added to the mixture, which was then heated at 80° C. overnight. The reaction mixture was cooled to rt, and then filtered through a pad of Celite®, rinsing with ethyl acetate. The organic layer was separated, washed with water and brine, and dried (Na2SO4). The solvent was removed by rotary evaporation, and the solid residue was purified by using a Biotage QuadUV flash chromatography system (eluant: 3:1 hexane/EtOAc). The product 3-(4′-amino-biphenyl-4-carbonyl)-cyclohexanecarboxylic acid methyl ester was obtained as a brown solid (200 mg, yield 38.5%). 1H NMR (300 MHz, DMSO) δ 7.90 (d, 2H), 7.60 (d, 2H), 7.45 (d, 2H), 6.80 (d, 2H), 3.70 (s, 3H), 3.25 (m, 1H), 2.50 (m, 1H), 2.20-1.90 (m, 4H), 1.70-1.50 (m, 4H); LC-MS ret. time 3.80 nm in (method 2), m/z 338.17 (MH+).

후처리

  1. customthe mixture was degassed
  2. customby bubbling with a flow of argon for 45 minutes
  3. temperatureThe reaction mixture was cooled to rt
  4. filtrationfiltered through a pad of Celite®
  5. washrinsing with ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried (Na2SO4)
  9. customThe solvent was removed by rotary evaporation
  10. customthe solid residue was purified

출처 및 근거

ORD 기록
ord-8dbb215034d44fd389920ef1555fed66
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013166B2

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