Sodium Carbonate → 3-(5,6-dihydro-2H-pyran-3-yl)-2-fluoropyridine

HRID 1880095ノート

反応式

HRID 1880095 の反応式
C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)S(O[C:13]1[CH2:14][O:15][CH2:16][CH2:17][CH:18]=1)(=O)=O.[F:21][C:22]1[C:27](B(O)O)=[CH:26][CH:25]=[CH:24][N:23]=1>COCCOC.CCOC(C)=O.O.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>[O:15]1[CH2:16][CH2:17][CH:18]=[C:13]([C:27]2[C:22]([F:21])=[N:23][CH:24]=[CH:25][CH:26]=2)[CH2:14]1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 593272465,6-dihydro-2H-pyran-3-yl trifluoromethanesulfonate

生成物 1

HCID 593270283-(5,6-dihydro-2H-pyran-3-yl)-2-fluoropyridine

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

Sodium carbonate (29.0 mL, 58.0 mmol, 2.0 M in water) was added via syringe to a stirred mixture of 5,6-dihydro-2H-pyran-3-yl trifluoromethanesulfonate (4.49 g, 19.3 mmol), 2-fluoropyridine-3-boronic acid (2.72 g, 19.3 mmol), and tetrakis(triphenylphosphine)palladium (1.12 g, 0.97 mmol) in DME (82 mL) under an argon atmosphere. The reaction mixture was stirred at 80° C. for 17 h. The reaction mixture was then cooled to room temperature before being diluted with EtOAc and water. The organic layer was separated, washed with sat. aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography to give 3-(5,6-dihydro-2H-pyran-3-yl)-2-fluoropyridine. MS (ESI, pos. ion) m/z: 180.0.

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with sat. aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-abbfbd45ef2a441d8a62d28d4fb03770
出典データセット
uspto-grants-2012_11
特許番号
US08318718B2

反応ノート

読み込み中…