Cesium carbonate → 2-Chloro-5-(2-fluorophenyl)pyrimidine

HRID 630450노트

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HRID 630450 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:9]=[N:10][C:11]([Cl:14])=[N:12][CH:13]=1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>O1CCOCC1.O.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>[Cl:14][C:11]1[N:10]=[CH:9][C:8]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[F:15])=[CH:13][N:12]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 27343542-Fluorophenylboronic acid

생성물 1

HCID 463120562-Chloro-5-(2-fluorophenyl)pyrimidine

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 218864351,4-Dioxane--water (1/1)용매

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온도
90 °C

실험 절차

Tetrakis(triphenylphosphine)palladium(0) (2.06 g, 1.79 mmol, 0.1 eq) and caesium carbonate (17.4 g, 53.69 mmol, 2.0 eq) were added under an argon atmosphere to a stirred solution of 5-bromo-2-chloropyrimidine (2.5 g, 17.86 mmol, 1 eq) and (2-fluorophenyl)boronic acid (3.45 g, 17.86 mmol, 1.0 eq) in 1,4-dioxane/water (30 mL, 4:1) at room temperature. The mixture was heated to 90° C., stirred for 3 h and then cooled to room temperature. The mixture was diluted with ethyl acetate (10 mL), washed with water, and dried over sodium sulfate. The solvents were removed in vacuo and the residue was purified by column chromatography [silica gel 100-200 mesh, ethyl acetate/petrolether 1:19]. Yield: 2.0 g (53% of theory)

후처리

  1. temperaturecooled to room temperature
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvents were removed in vacuo
  5. customthe residue was purified by column chromatography [silica gel 100-200 mesh, ethyl acetate/petrolether 1:19]

출처 및 근거

ORD 기록
ord-e70763ec27fa4758a25dec7d0d2afb8a
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315490B2

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