Ethyl Acetate → 2-(5-Bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzaldehyde

HRID 554614노트

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HRID 554614 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:10]=2[CH:11]=[O:12])O1.Br[C:23]1[C:24]([O:30][CH3:31])=[N:25][CH:26]=[C:27]([Br:29])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>COCCOC.O.[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:29][C:27]1[CH:28]=[C:23]([C:9]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][C:10]=2[CH:11]=[O:12])[C:24]([O:30][CH3:31])=[N:25][CH:26]=1

참가 물질

9

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 135677523,5-Dibromo-2-methoxypyridineHCID 866405342-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzaldehyde

생성물 1

HCID 866405372-(5-Bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzaldehyde

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 57417360Sodium chloride; water용매

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온도
85 °C

실험 절차

2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzaldehyde (1.59 g, 4.4 mmol), 3,5-dibromo-2-methoxy-pyridine (1.19 g, 4.4 mmol), and potassium carbonate (2.17 g, 15.6 mmol) were combined in DME (13 mL) and H2O (6 mL). The solution was purged with N2 for 30 minutes, and dichlorobis(triphenylphosphine)palladium(II) (0.156 g, 0.22 mmol) was added. The reaction was stirred at 85° C. overnight, and then cooled to room temperature and worked-up with EtOAc and brine. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give 2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzaldehyde, which was repurified by preparative HPLC.

후처리

  1. customThe solution was purged with N2 for 30 minutes
  2. temperaturecooled to room temperature
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-85432fc2f6f240acabdb14bcdaab98d6
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08049015B2

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