Potassium Carbonate → 2-(4-Benzoimidazol-1-yl-phenyl)-3-methyl-3H-imidazole-4-carboxylic acid methyl ester

HRID 1716867노트

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HRID 1716867 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[N:17]=[CH:16]3)=[CH:11][CH:10]=2)O1.[CH3:25][O:26][C:27]([C:29]1[N:30]([CH3:35])[C:31](Br)=[N:32][CH:33]=1)=[O:28].C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(OCC)(=O)C.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>[CH3:25][O:26][C:27]([C:29]1[N:30]([CH3:35])[C:31]([C:9]2[CH:10]=[CH:11][C:12]([N:15]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[N:17]=[CH:16]3)=[CH:13][CH:14]=2)=[N:32][CH:33]=1)=[O:28]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 26343677Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylateHCID 575501981-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-benzoimidazole

생성물 1

HCID 575502252-(4-Benzoimidazol-1-yl-phenyl)-3-methyl-3H-imidazole-4-carboxylic acid methyl ester수율 36%

시약·촉매·용매 3

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

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온도
90 °C

실험 절차

To a solution of 1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-benzoimidazole (0.43 g, 1.5 mmol) and 2-bromo-3-methyl-3H-imidazole-4-carboxylic acid methyl ester (0.25 g, 1.15 mmol) in DME (9 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.07 g, 0.057 mmol) and 2 M aqueous potassium carbonate (1.4 mL) and the reaction mixture was heated at 90° C. for 12 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The reaction mixture was filtered and the filtrate washed with water, dried (Na2SO4), and the solvent removed under reduced pressure. Purification by flash column chromatography (silica, petroleum ether:ethyl acetate 7:3→1:1 then dichloromethane:methanol 99:1→97:3) provided the title compound (36%). LCMS (ESI+) 332.2 (MH+).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate washed with water
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed under reduced pressure
  6. customPurification by flash column chromatography (silica, petroleum ether:ethyl acetate 7:3→1:1

출처 및 근거

ORD 기록
ord-28bb855d7b6941de8b267504ab1dcb10
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803825B2

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