Sodium Carbonate → 3-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine

HRID 410209ノート

反応式

HRID 410209 の反応式
Br[C:2]1[C:3]([F:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[O:9]1[CH2:14][CH:13]=[C:12](B2OC(C)(C)C(C)(C)O2)[CH2:11][CH2:10]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[O:9]1[CH2:10][CH:11]=[C:12]([C:2]2[C:3]([F:8])=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:14]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27627783-Bromo-2-fluoropyridineHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

生成物 1

HCID 593267823-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

To a round bottomed flask was added 3-bromo-2-fluoropyridine (5.2201 g, 29.7 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.79 g, 37.1 mmol), trans-dichlorobis(triphenylphosphine) palladium (II) (1.666 g, 2.373 mmol), and sodium carbonate (15.72 g, 148 mmol) in DME (47.5 mL) and Water (11.86 mL) to stir at 80° C. overnight. Reaction was allowed to cool to room temperature. The reaction mixture was diluted with water and extracted with DCM. The organic extract was washed with water, brine, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (40M), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide 3-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine. MS (ESI, pos. ion) m/z: 180.1 (M+1).

後処理

  1. customReaction
  2. temperatureto cool to room temperature
  3. extractionextracted with DCM
  4. extractionThe organic extract
  5. washwas washed with water, brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed through a Biotage pre-packed silica gel column (40M)
  10. washeluting with a gradient of 10% to 100% EtOAc in hexane

出典と根拠

ORDレコード
ord-ef0870f031764aa282b45a543c4fc82b
出典データセット
uspto-grants-2014_06
特許番号
US08759532B2

反応ノート

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