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

HRID 630450ノート

反応式

HRID 630450 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
90 °C

実験手順

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)

後処理

  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]

出典と根拠

ORDレコード
ord-e70763ec27fa4758a25dec7d0d2afb8a
出典データセット
uspto-grants-2016_04
特許番号
US09315490B2

反応ノート

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